tert-Butyl mercaptan → 2-(Tert-Butylthio)Benzaldehyde

HRID 1893131Notes

Reaction equation

HRID 1893131 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]([SH:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([S:20][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:19])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 11430Potassium Carbonate2×HCID 67970o-Fluorobenzaldehyde

Product 1

HCID 27769202-(Tert-Butylthio)BenzaldehydeYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-fluoro-benzaldehyde (2.00 g, 16.1 mmol), potassium carbonate (2.45 g, 17.7 mmol) and 2-methyl-2-propanethiol (17.1 mmol) were dissolved in 10.0 mL DMF in a 50 mL round-bottomed flask under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 50° C. for 4 days. After cooling, the mixture was added to 50 ml of saturated potassium carbonate solution and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 2:1 dichloromethane/n-hexane as eluent to give a yellow oil (1.26 g, 40%). 1H NMR (200 MHz, CDCl3): δ 1.26 (s, 9H), 7.43-7.63 (m, 3H), 7.96 (dd, J1=6.9, J2=2.5, 1H), 10.76 (s, 1H) ppm.

Workup

  1. customtopped with a reflux condenser
  2. temperatureAfter cooling
  3. extractionextracted with 3×50 mL portions of ether
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. customevaporated
  6. customThe crude product was further purified by chromatography on silica gel using 2:1 dichloromethane/n-hexane as eluent

Sources & evidence

ORD record
ord-9ad6923de6ad4d51974c0cabf07c0e64
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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