Bromotrimethylsilane → 4'-Bromomethyl-4-methanesulfonyl-biphenyl

HRID 724624Notes

Reaction equation

HRID 724624 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:19][Si](C)(C)C>O1CCOCC1>[Br:19][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 21878562[4'-(Methylsulfonyl)[1,1'-biphenyl]-4-yl]methanol

Product 1

HCID 218788684'-Bromomethyl-4-methanesulfonyl-biphenylYield 95.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (4′-methanesulfonyl-biphenyl-4-yl)-methanol (129 mg, 0.49 mmol) in 1,4-dioxane (5 mL) was treated with bromotrimethylsilane (0.2 mL, 1.5 mmol) and stirred at 25° C. for 16 h. The reaction mixture was concentrated and purified by flash column chromatography to yield 4.15-B (152 mg, 95%) as a yellow solid. LCMS found for C14H14BrO2S (M+H)+: m/z=326.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-f82444c3665140e58266c7d4a8ed0068
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

Loading…