Water → 3-Bromo-2-(tert-butylthio)-4-iodobenzaldehyde

HRID 389475Notes

Reaction equation

HRID 389475 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]([SH:22])([CH3:21])[CH3:20].O>CN(C=O)C>[Br:1][C:2]1[C:3]([S:22][C:19]([CH3:21])([CH3:20])[CH3:18])=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 866624033-Bromo-2-fluoro-4-iodobenzaldehyde

Product 1

HCID 866624043-Bromo-2-(tert-butylthio)-4-iodobenzaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-2-fluoro-4-iodo-benzaldehyde (1.3 g, 4.0 mmol), potassium carbonate (0.66 g, 4.7 mmol), and 2-methylpropane-2-thiol (0.53 mL, 4.7 mmol) in dry DMF (2 mL) was heated at 80° C. in a sealed tube for 16 h. The reaction mixture was cooled to RT, water was added, and the mixture was extracted with dichloromethane (2×30 mL). The combined organic fractions were washed with water (60 mL), dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (5% ethyl acetate:hexanes) afforded 1.0 g (64%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.30 (s, 9H), 7.54 (d, J=8.1 Hz, 1H), 7.87 (d, J=8.1 Hz, 1H), 10.29 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthe mixture was extracted with dichloromethane (2×30 mL)
  3. washThe combined organic fractions were washed with water (60 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by column chromatography (5% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-3df3a2e646dd4600a47f956f67291a05
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…