2,2,2-Trifluoroethanethiol → HCID 58372815, compound

HRID 888530Notes

Reaction equation

HRID 888530 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[CH2:23]Br)[CH:7]=1)[CH3:2].[F:26][C:27]([F:31])([F:30])[CH2:28][SH:29]>>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[CH2:23][S:29][CH2:28][C:27]([F:31])([F:30])[F:26])[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 41339242,2,2-TrifluoroethanethiolHCID 58372796[3-(2-Bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]acetic acid ethyl ester

Product 1

HCID 58372815HCID 58372815, compound

Procedure

As described for Example 21, [3-(2-bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]acetic acid ethyl ester and 2,2,2-trifluoroethanethiol were reacted to provide {4-chloro-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester, which was reduced to the amine and then treated with pivaloyl chloride to provide {4-chloro-3-[4-(2,2-dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester provided the acid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5f89ff4804b0410a9e299f034f35d79a
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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