Bromotrimethylsilane → 4-(Bromomethyl)-1-methoxy-2-(3-methoxypropoxy)benzene

HRID 264944Notes

Reaction equation

HRID 264944 reaction equation
C[Si](C)(C)[Br:3].[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]O)=[CH:10][C:9]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21]>C(Cl)(Cl)Cl>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][Br:3])=[CH:10][C:9]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Product 1

HCID 115583294-(Bromomethyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

97 ml of trimethylbromosilane are added, with stirring at room temperature, to 113.1 g of 4-methoxy-3-(3-methoxypropyloxy)-benzyl alcohol in 1.31 litres of chloroform. After 10 minutes the solvent is evaporated off and the residue is immediately purified by means of FC (900 g of silica gel, eluant: ethyl acetate/hexane 1:3). The title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.34; m.p. 50°-51° C.

Workup

  1. customAfter 10 minutes the solvent is evaporated off
  2. customthe residue is immediately purified by means of FC (900 g of silica gel, eluant: ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-86a613c75a2d41b89d4db6666d30748d
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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