Triphenylphosphine → 1-Bromo-3-(bromomethyl)-5-methoxybenzene

HRID 2069077Notes

Reaction equation

HRID 2069077 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:22]=[C:23]([CH2:29]O)[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1.[Br:31]N1C(=O)CCC1=O>ClCCl>[Br:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([CH2:29][Br:31])[CH:22]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 10608788(3-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzeneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (28 g; KANTO) was added to a dichloromethane (150 mL) solution of Intermediate 1 (22.05 g) with ice cooling, the resulting mixture was stirred for approx. 10 minutes followed by the addition of N-bromosuccinimide (20 g; TCI), and the resulting mixture was stirred at room temperature for 13 hours and 30 minutes. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (n-hexane/ethyl acetate) to give the title compound (23.94 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 13 hours and 30 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5db04305b639489cbdb098cef07443bb
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

Loading…