2-Thiocresol → Ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate

HRID 2177744Notes

Reaction equation

HRID 2177744 reaction equation
[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:10](CSC2C=CC=CC=2)=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].[C:31](=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:31][S:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH3:23])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 87122-ThiocresolHCID 11430Potassium CarbonateHCID 67107500HCID 67107500, compound2×

Product 1

HCID 67107587Ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-bromo-6-bromomethyl-2-methoxybenzoate (Intermediate 87, 0.262 g), 2-methylthiophenol (0.096 ml) and potassium carbonate (0.28 g) in THF (5 ml) was stirred at room temperature for 3 days. The resultant mixture was partitioned between ethyl acetate and NaHCO3 (saturated aqueous solution). The separated organic phase was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give ethyl 3-bromo-2-methoxy-(2-methylphenylthiomethyl)benzoate (0.24 g) as a gum.

Workup

  1. customThe resultant mixture was partitioned between ethyl acetate and NaHCO3 (saturated aqueous solution)
  2. dry with materialThe separated organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

Sources & evidence

ORD record
ord-32c34a0988db45668196eeeec70cdda5
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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