Water → 3-Bromo-2-(tert-butylthio)benzaldehyde

HRID 389436

Reaction equation

HRID 389436 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([SH:21])([CH3:20])[CH3:19].O>CN(C=O)C>[Br:1][C:2]1[C:3]([S:21][C:18]([CH3:20])([CH3:19])[CH3:17])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 220193613-Bromo-2-fluorobenzaldehyde

Product 1

HCID 866623973-Bromo-2-(tert-butylthio)benzaldehydeYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-bromo-2-fluorobenzaldehyde (5.0 g, 25 mmol), potassium carbonate (4.0 g, 30 mmol) and 2-methyl-2-propanethiol (5.5 mL, 49 mmol) in dry DMF (25 mL) was heated to 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, added to water (100 mL) and extracted with DCM (3×50 mL). The combined organic fractions were washed with water (50 mL), dried, and evaporated to afford 6.7 g (98%) of the crude title compound which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 1.31 (s, 9H), 7.26-7.41 (m, 1H), 7.93-7.99 (m, 2H), 10.73 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with DCM (3×50 mL)
  3. washThe combined organic fractions were washed with water (50 mL)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9356c753a1e344abb506c2b0a4d487a4
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Linked notes

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