Anisole → Methyl 2-mercapto-5-trifluoromethylbenzoate

HRID 978084Notes

Reaction equation

HRID 978084 reaction equation
COC1C=CC(C[S:8][C:9]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[SH:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 20205034Methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate

Product 1

HCID 13787739Methyl 2-mercapto-5-trifluoromethylbenzoate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate (1.0 g, 2.8 mmol) and anisole (335 μl) in trifluoroacetic acid (10 ml) was stirred at reflux temperature for 20 minutes under a nitrogen atmosphere. The mixture was evaporated under diminished pressure and co-evaporated several times with toluene. The mercaptan was used without further purification in the subsequent step below. NMR (CDCl3, 60 MHz): δ3.88 (s, CO2CH3) p.p.m.

Workup

  1. temperatureat reflux temperature for 20 minutes under a nitrogen atmosphere
  2. customThe mixture was evaporated under diminished pressure and co-evaporated several times with toluene
  3. customThe mercaptan was used without further purification in the subsequent step below

Sources & evidence

ORD record
ord-ef885c99173b4eafba90deed7949a4f7
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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