Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate → 1-Chloro-2-fluoro-4-methoxy-3-(trifluoromethyl)benzene

HRID 2178713Notes

Reaction equation

HRID 2178713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10].ClC1C=CC(OC)=C(I)C=1[F:21].[F:22][C:23]([F:32])(S(F)(=O)=O)C(OC)=O>[Cu](I)I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:23]([F:32])([F:21])[F:22])[C:3]=1[F:10]

Participants

5

Reactant 3

HCID 547667Methyl 2,2-difluoro-2-(fluorosulfonyl)acetateHCID 27245211-Chloro-2-fluoro-4-methoxybenzeneHCID 683801001-Chloro-2-fluoro-3-iodo-4-methoxybenzene2×

Product 1

HCID 683807301-Chloro-2-fluoro-4-methoxy-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

1-Chloro-2-fluoro-4-methoxybenzene was converted to 1-chloro-2-fluoro-3-iodo-4-methoxybenzene (see G. L. Grunewald et al., J. Med. Chem. 1986, 29, 1972-1982). 1-Chloro-2-fluoro-3-iodo-4-methoxybenzene was treated with methyl difluoro(fluorosulfonyl)acetate in the presence of copper iodide (A. Khilevich et al., U.S. Pat. Appl. Publ. 2010, US 20100016373) to provide 1-chloro-2-fluoro-4-methoxy-3-(trifluoromethyl)benzene. 4-Chloro-3-fluoro-2-(trifluoromethyl)phenol was then obtained by de-methylation using boron trichloride.

Sources & evidence

ORD record
ord-2688e207687b4d0bb4983e61e6354074
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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