Boron tribromide → 4-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]-phenol

HRID 1945186Notes

Reaction equation

HRID 1945186 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([S:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:7]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([S:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH2:24][CH3:25])(=[O:22])=[O:23])=[CH:19][CH:20]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 669957324-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]-1-methoxy-benzene

Product 1

HCID 669960804-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron tribromide (1M in DCM, 2.3 ml) was slowly added to a stirred solution of the product from step (ii) (0.4 g) in DCM (20 ml) at 0° C. After 0.5 h a further 4 ml of boron tribromide solution was added and the mixture stirred for 1 h. The reaction was quenched with crushed ice and partitioned between water and DCM. The organics separated, dried, and evaporated under reduced pressure, yield 0.3 g.

Workup

  1. customThe reaction was quenched with crushed ice
  2. custompartitioned between water and DCM
  3. customThe organics separated, dried
  4. customevaporated under reduced pressure, yield 0.3 g

Sources & evidence

ORD record
ord-affccc85f2cd4de38ece9721734efd1c
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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