Water → HCID 24824646, compound

HRID 2220398Notes

Reaction equation

HRID 2220398 reaction equation
[H-].[Na+].[CH3:3][CH:4]([SH:6])[CH3:5].[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10](F)[CH:9]=1.O>CS(C)=O>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([S:6][CH:4]([CH3:5])[CH3:3])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 24824646HCID 24824646, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (32.87 g) in dimethyl sulfoxide (600 ml) was added 2-propanethiol (41.73 ml) at ° C. under nitrogen atmosphere and stirred at room temperature for 1 hour. The reaction mixture was cooled with ice bath and added 4-bromo-2-fluorobenzoic acid (60 g). The reaction mixture was stirred at 70° C. for 1.5 hours and then cooled to room temperature. The mixture was poured into water (3 l) and washed with hexane (600 ml). The water layer was acidified with concentrated hydrochloric acid and then the resulting white solid was collected by filtration. The white solid was dried at 60° C. to give 4-bromo-2-(isopropylthio)benzoic acid (75.49 g).

Workup

  1. temperatureThe reaction mixture was cooled with ice bath
  2. stirringThe reaction mixture was stirred at 70° C. for 1.5 hours
  3. temperaturecooled to room temperature
  4. washwashed with hexane (600 ml)
  5. filtrationthe resulting white solid was collected by filtration
  6. customThe white solid was dried at 60° C.

Sources & evidence

ORD record
ord-c333035b3d994839ac48b88966efdaa6
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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