Boron tribromide → HCID 69007099, compound

HRID 1432041Notes

Reaction equation

HRID 1432041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[C:4]([O:16]C)[CH:3]=1.B(Br)(Br)Br>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[C:4]([OH:16])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69006946HCID 69006946, compound

Product 1

HCID 69007099HCID 69007099, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-chloro-1-(3-fluoro-phenylsulfanyl)-2-methoxybenzene (3.12 g, 11.6 mmol) in dry toluene (60 mL) was cooled to 0° C. Neat BBr3 (1.50 mL, 15.9 mmol) was added dropwise and the mixture was allowed to reach room temperature overnight. The mixture was quenched by the addition of H2O/ice (50 mL) and diethyl ether (50 mL). The aqueous layer was extracted with diethylether (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and adsorbed onto silica gel. After flash chromatography using silica gel, eluting with heptanes/EtOAc, 95:5, the title compound was obtained as a light yellow oil (2.26 g, 77%).

Workup

  1. customThe mixture was quenched by the addition of H2O/ice (50 mL) and diethyl ether (50 mL)
  2. extractionThe aqueous layer was extracted with diethylether (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. washeluting with heptanes/EtOAc, 95:5

Sources & evidence

ORD record
ord-aa66aee616cc40f6ba5ca1087e94cc86
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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