Benzyl mercaptan → HCID 89444802, compound

HRID 1522771Notes

Reaction equation

HRID 1522771 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:33])/[CH:19]=[C:20](\[C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)/[C:21]([F:24])([F:23])[F:22])=[CH:14][C:13]=1[CH3:34]>O1CCCC1>[CH2:1]([S:8][C:20]([C:25]1[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=1)([C:21]([F:22])([F:23])[F:24])[CH2:19][C:18]([C:15]1[CH:16]=[CH:17][C:12]([Br:11])=[C:13]([CH3:34])[CH:14]=1)=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptan2×HCID 14798Sodium Hydroxide2×HCID 72735842HCID 72735842, compound

Product 1

HCID 89444802HCID 89444802, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzylmercaptan (0.18 g) and a solution of sodium hydroxide (0.1 eq) were added to a solution of (E)-1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-1-one (0.5 g) in tetrahydrofurane (11.4 mL). The solution was stirred at room temperature for 19 hours then heated at 80° C. for 4 hours. Then, more benzylmercaptan (0.5 mL) was added and the solution was stirred at 80° C. for 16 hours. More sodium hydroxide (20 mg) was added and after 90 minutes, the reaction was quenched by the addition of a saturated solution of sodium chloride, and then extracted with diethyl ether. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give 3-Benzylsulfanyl-1-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butan-1-one (276 mg).

Workup

  1. temperaturethen heated at 80° C. for 4 hours
  2. stirringthe solution was stirred at 80° C. for 16 hours
  3. customthe reaction was quenched by the addition of a saturated solution of sodium chloride
  4. extractionextracted with diethyl ether
  5. dry with materialThe collected organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated under vacuo
  8. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-7cb9bc2e25c74e7d98d41afbc0c1b939
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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