Oxygen → 2-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906515Notes

Reaction equation

HRID 906515 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]=C)[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17](=[O:19])[CH3:18].[O:21]=[O+][O-].O=O.CSC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]=[O:21])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17](=[O:19])[CH3:18]

Participants

7

Reactant 5

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 11776TriphenylphosphineHCID 24823OzoneHCID 59164494HCID 59164494, compound

Product 1

HCID 591644232-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-acetylamino-4-trifluoromethyl-5-vinyl-benzoic acid methyl ester (708 mg, 2.46 mmol) in DCM (70 mL) was cooled to −68° C. and a flow of ozone was passed through the mixture until it turned dark green. A flow of oxygen was then passed through the mixture for 30 min and dimethyl sulfide (360 μL, 4.86 mmol) was added. This mixture was stirred for 30 min at r.t. and triphenylphosphine (327 mg, 1.23 mmol) was added. The solution was allowed to stand for 60 h at r.t. under argon. It was then concentrated in vacuo and the crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 100:0→80:20) to afford 2-acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester (591 mg, 2.04 mmol, 83%) as a beige powder, m.p. 106-108° C., ESI-MS: m/z 290 [M+H]+.

Workup

  1. waitto stand for 60 h at r.t. under argon
  2. concentrationIt was then concentrated in vacuo
  3. customthe crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 100:0→80:20)

Sources & evidence

ORD record
ord-06fb66aead2d4e6eba6bf2e2842ec442
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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