Water → HCID 85859821, compound

HRID 1880428Notes

Reaction equation

HRID 1880428 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].O>CC(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:15][C:12]([CH3:14])([CH3:13])[CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 85859821HCID 85859821, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (4.06 g) in 2-propanol (20.0 mL) was added 2-methyl-2-propanethiol (2.26 mL) and K2CO3 (3.04 g) and heated overnight. The reaction mixture was cooled to room temperature, poured into 50.0 mL water and extracted with dichloromethane. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was flash chromatographed (3% EtOAc/Haptanes) to obtain 1.97 g (36%) of 5-bromo-2-(tert-butylthio)benzaldehyde as a clear oil. 1H NMR (500 MHz, CDCl3) 8 ppm 1.30 (s, 9 H) 7.51 (d, J=8.05 Hz, 1 H) 7.70 (dd, J=8.29, 2.20 Hz, 1 H) 8.12 (d, J=2.20 Hz, 1 H) 10.70 (s, 1 H).

Workup

  1. temperatureheated overnight
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed (3% EtOAc/Haptanes)

Sources & evidence

ORD record
ord-b0ae68a8a2204736b7b8010dd7bf2a2d
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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