Water → 3-Bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde

HRID 389467Notes

Reaction equation

HRID 389467 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]([SH:24])([CH3:23])[CH3:22].O>CN(C=O)C>[Br:1][C:2]1[C:3]([S:24][C:21]([CH3:23])([CH3:22])[CH3:20])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 866624013-Bromo-2-fluoro-5-nitrobenzaldehyde

Product 1

HCID 866624003-Bromo-2-tert-butylsulfanyl-5-nitro-benzaldehydeYield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-bromo-2-fluoro-5-nitro-benzaldehyde (1.0 g, 4 mmol), potassium carbonate (667 mg, 4.8 mmol) and 2-methyl-2-propanethiol (326 mg, 0.40 mL, 3.6 mmol) in dry DMF (5 mL) was heated at 110° C. in a sealed tube for 16 h. The reaction was cooled to RT, water was added, and the mixture extracted with dichloromethane (2×30 mL). The combined organic fractions were washed with water (3×15 mL), dried over sodium sulfate, filtered and concentrated to afford 1.2 g of the crude title compound, which was used without further purification.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionthe mixture extracted with dichloromethane (2×30 mL)
  3. washThe combined organic fractions were washed with water (3×15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c4fecd2afb640f0bd8d512cea9bed19
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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