Fluorinated organic compound production method

A method for producing a fluorinated organic compound, comprising:

• step A of fluorinating an organic compound (1) by reaction with a fluorine source (3)
• in the presence of a hypervalent iodine aromatic ring compound (2a), or
• in the presence of an iodine aromatic ring compound (2b) and an oxidant (2bo);
• wherein the fluorine source (3) is a fluorine source (3a) represented by formula:
• MFn, wherein M is H, a metal of Group 1 of the periodic table, or a metal of Group 2 of the periodic table;
• and n is 1 or 2;
• step B of separating the iodine aromatic ring compound from a reaction liquid after step A is started;
• and
• step C of oxidizing the iodine-substituted aromatic ring compound separated from the reaction liquid in step B with an oxidant (C),
• wherein the organic compound (1) is:
• an organic compound represented by formula (1a):
• wherein
• A is a hydrogen atom, an aromatic group optionally having one or more substituents, an alkyl group optionally having one or more substituents, a halogen atom, —OR, or —NR2,
• R1 is a hydrogen atom, an organic group, or a halogen atom,
• R2 is a hydrogen atom, an organic group, or a halogen atom, and
• R is independently at each occurrence a hydrogen atom or an organic group;
• or
• an organic compound represented by formula (1b):
• wherein
• R3 is a hydrogen atom, an aromatic group optionally having one or more substituents, an alkyl group optionally having one or more substituents, a halogen atom, —OR, or —NR2,
• R4 is a hydrogen atom, an aromatic group optionally having one or more substituents, an alkyl group optionally having one or more substituents, a halogen atom, —OR, or —NR2,
• R5 is a hydrogen atom, an aromatic group optionally having one or more substituents, an alkyl group optionally having one or more substituents, a halogen atom, —OR, or —NR2, and
• R is independently at each occurrence a hydrogen atom or an organic group;
• and
• wherein the hypervalent iodine aromatic ring compound (2a) is an organic compound represented by formula (2a1):
• wherein
• Ar is an aromatic ring,
• Rp1 is independently at each occurrence
• a group:
• —O—(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a group:
• —(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a group:
• —O—(CH2)q-A, wherein q is a number greater than or equal to 1;
• A is —SO3Y or —COOY;
• Y is independently at each occurrence H, a metal atom, or NR54;
• and R5 is independently at each occurrence H or an organic group,
• a group:
• —(CH2)q-A, wherein q is a number greater than or equal to 1;
• A is —SO3Y or —COOY;
• Y is independently at each occurrence H, a metal atom, or NR54;
• and R5 is independently at each occurrence H or an organic group,
• a carboxylic acid group, or
• a sulfonic acid group;
• Rp2 is independently at each occurrence
• an alkyl group,
• an alkoxy group,
• a group:
• —O—(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a group:
• —(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a halogen atom,
• a cyano group,
• a nitro group,
• a carboxylic acid group,
• a sulfonic acid group,
• a hydroxy group, or
• a phosphoryloxy group;
• or
• two Rp2 bonded to one iodine atom optionally together form ═O;
• n1 is a number greater than or equal to 1;
• n2 is a number greater than or equal to 1;
• and
• the sum of n1 and n2 is in the range of 2 to 11;
• and
• the iodine aromatic ring compound (2b) is an organic compound represented by formula (2b1):
• wherein
• Ar is an aromatic ring;
• Rp1 is independently at each occurrence
• a group:
• —O—(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a group:
• —(CH2)q—NR3X, wherein q is a number greater than or equal to 1;
• R is H or a C1-C20 alkyl group;
• and X is a halogen atom, an arylsulfonyloxy group, or an alkylsulfonyloxy group,
• a group:
• —O—(CH2)q-A, wherein q is a number greater than or equal to 1;
• A is —SO3Y or —COOY;
• Y is independently at each occurrence H, a metal atom, or NR54;
• and R5 is independently at each occurrence H or an organic group,
• a group:
• —(CH2)q-A, wherein q is a number greater than or equal to 1;
• A is —SO3Y or —COOY;
• Y is independently at each occurrence H, a metal atom, or NR54;
• and R5 is independently at each occurrence H or an organic group,
• a carboxylic acid group, or
• a sulfonic acid group;
• n1 is a number greater than or equal to 1;
• n2 is a number greater than or equal to 1;
• and
• the sum of n1 and n2 is in the range of 2 to 11.