Benzyl Bromide → Benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate

HRID 2177865Notes

Reaction equation

HRID 2177865 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:23][CH3:24])=[C:8]([C:12]([CH2:15][S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:2]1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:23][CH3:24])=[C:8]([C:12]([CH2:15][S:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)[C:9]([O:11][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:10])=[CH:2]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 671080273-(Furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid2×

Product 1

HCID 67107722Benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoateYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid (Intermediate 223, 0.83 g), benzyl bromide (0.46 g) and potassium carbonate (0.55 g) in THF (15 ml) was heated to 60° C. for 8 hours. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-10% to give benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)-benzoate (0.96 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-10%

Sources & evidence

ORD record
ord-aa75b827b2c94b7e87494ad912cdb2dd
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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