Ethyl trifluoroacetate → 2,2-Diphenyl-6-(trifluoroacetyl)-1,3-benzodioxole-4-carboxylic acid

HRID 2251595Notes

Reaction equation

HRID 2251595 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.O(C)[Li].[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32]>>[C:10]1([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:7][C:6]3[CH:22]=[C:2]([C:31](=[O:32])[C:30]([F:37])([F:36])[F:29])[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]=3[O:9]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 596429946-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acidHCID 178419045HCID 178419045, compound

Product 1

HCID 596430032,2-Diphenyl-6-(trifluoroacetyl)-1,3-benzodioxole-4-carboxylic acid

Procedure

6-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid (200 mg, 0.503 mmol, 1 eq.), LiOMe (40 mg, 1 mmol, 2 eq.) and ethyl trifluoroacetate (0.6 mL, 5.03 mmol, 10 eq.) as the electrophile were reacted according to GP4, Method A. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc/AcOH 77:20:3) to give the title compound as a yellowish solid.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-8226db667858473c90a43dda8fe6ace9
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

Loading…