Triphenylphosphine → 1,1'-Biphenyl, 4-(bromomethyl)-

HRID 2185495Notes

Reaction equation

HRID 2185495 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.O[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1>ClCCl>[C:36]1([C:33]2[CH:34]=[CH:35][C:30]([CH2:29][Br:20])=[CH:31][CH:32]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 19186(1,1'-Biphenyl)-4-methanolHCID 67184N-bromobutanimide

Product 1

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-Yield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.58 g) and N-bromosuccinimide (1.07 g) were added to a stirred solution of 4-hydroxymethylbiphenyl (1.01 g) in dichloromethane (10 mL) under nitrogen. The mixture was stirred at room temperature for 15 hr and evaporated in vacuo. The residue was diluted with chloroform, and washed with saturated sodium hydrogencarobonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:100 to 1:50, v/v) to give the titled compound (1.26 g) as colorless crystals: 1H-NMR (400 MHz, CDCl3) δ 4.55 (s, 2H), 7.33-7.38 (m, 1H), 7.41-7.49 (m, 4H), and 7.54-7.60 (m, 4H).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with chloroform
  3. washwashed with saturated sodium hydrogencarobonate, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-8c5c6a482f9041288beb5ce4dcad89af
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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