Water → 4-Bromo-2-fluorobenzene-1-thiol

HRID 1023771Notes

Reaction equation

HRID 1023771 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=O)=O)=[C:23]([F:31])[CH:22]=1.O>C1COCC1>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[C:23]([F:31])[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 225069554-Bromo-2-fluorobenzene-1-thiolYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Triphenylphosphine was added portionwise to a solution of 4-bromo-2-fluorobenzenesulfonyl chloride (8.44 g) in THF (30 ml) at 0° C. After 15 min water was added and the colourless solution was stirred at 20° C. for 18 h. The solvent was removed in vacuo, the residues dissolved in DCM and extracted with 2M sodium hydroxide (twice). The aqueous layers were washed with DCM, combined, acidified (4M HCl) and extracted with ethyl acetate (thrice). These organic extracts were dried (MgSO4) and evaporated to give the sub-title compound (5.89 g).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residues dissolved in DCM
  3. extractionextracted with 2M sodium hydroxide (twice)
  4. washThe aqueous layers were washed with DCM
  5. extractionextracted with ethyl acetate (thrice)
  6. dry with materialThese organic extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-42d67cefd17b4738991d6b1e6c7a1e18
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

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