Benzyl mercaptan → HCID 21099391, compound

HRID 2376940Notes

Reaction equation

HRID 2376940 reaction equation
CC(C)([O-])C.[K+].[CH:7]1[CH:12]=[CH:11][C:10]([CH2:13][SH:14])=[CH:9][CH:8]=1.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1F)=[O:17].[Cl-].[NH4+]>O1CCCC1>[CH2:13]([S:14][C:23]1[CH:22]=[C:21]([F:24])[CH:20]=[CH:19][C:18]=1[C:16](=[O:17])[CH3:15])[C:10]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 25517Ammonium ChlorideHCID 677702,4-DifluoroacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 21099391HCID 21099391, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (7.3 g, 65.1 mmol) was dissolved in tetrahydrofuran (250 mL) and benzylthiol (7.52 mL, 64.1 mmol) in tetrahydrofuran (40 mL) was added via syringe over 10 minutes. The thick suspension was stirred for 15 minutes before adding 2,4-difluoroacetophenone (10 g, 64.1 mmol). The reaction was stirred for 1 hour to give a deep red solution. Saturated aqueous ammonium chloride was added and the products extracted into ethyl acetate (×2). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was triturated with methanol to give 1-[2-(benzylthio)-4-fluorophenyl]ethanone (10.13 g, 61%).

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. customto give a deep red solution
  3. extractionthe products extracted into ethyl acetate (×2)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-4b03ad22048d4d88ad69a4167856c89f
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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