Triphenylphosphine → 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

HRID 2258285Notes

Reaction equation

HRID 2258285 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.[CH3:28][O:29][C:30]1[CH:42]=[CH:41][C:33]([CH2:34][C@H:35]([CH:38]([CH3:40])[CH3:39])[CH2:36]O)=[CH:32][C:31]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48]>ClCCl>[CH3:28][O:29][C:30]1[CH:42]=[CH:41][C:33]([CH2:34][C@H:35]([CH:38]([CH3:40])[CH3:39])[CH2:36][Br:20])=[CH:32][C:31]=1[O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 9835828(R)-2-[3-(3-Methoxypropoxy)-4-methoxybenzyl]-3-methylbutan-1-OL

Product 1

HCID 113258232-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzeneYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (108.6 g) and, in portions, N-bromosuccinimide (73.7 g) are added in succession at 0° C., with stirring, to a solution of 2(R)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methyl-butanol (102.2 g) in dichloromethane (2 liters). The batch is stirred for a further 18 hours at room temperature and is then concentrated under reduced pressure. The residue is purified by means of FC on silica gel (ethyl acetate/hexane 1:4). The title compound (102.2 g) is obtained in the form of a white solid: m.p. 52-53° C. (recrystallised from diethyl ether/hexane). Rf (ethyl acetate/hexane 1:1)=0.56. Anal. C17H27BrO3 (359.30): calc. C, 56.83; H, 7.57; Br, 22.24; found C, 56.81; H, 7.34; Br, 22.06.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. customThe residue is purified by means of FC on silica gel (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-435dae01995a41449c99bd930fb9eddc
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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