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

HRID 2258289Notes

Reaction equation

HRID 2258289 reaction equation
C[Si]([Br:5])(C)C.[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(OCC)(=O)C.CCCCCC>C(Cl)(Cl)Cl>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][Br:5])=[CH:10][C:9]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 21226206Ethyl acetate hexaneHCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trimethylsilyl bromide (97 ml) is added dropwise to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzyl alcohol (111.1 g) in chloroform (1.31 liters), the reaction temperature being maintained at 10°-25° C. by cooling with ice. When the addition is complete, the mixture is stirred for a further 10 minutes at room temperature and concentrated under reduced pressure. The residue is purified by FC on silica gel (ethyl acetate/hexane 1:3) and after recrystallisation from hexane the title compound (144.5 g) is obtained in the form of a white crystalline solid: m.p. 50-51° C. Rf (ethyl acetate/hexane 1:2)=0.34.

Workup

  1. temperaturethe reaction temperature being maintained at 10°-25° C.
  2. temperatureby cooling with ice
  3. additionWhen the addition
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by FC on silica gel (ethyl acetate/hexane 1:3)
  6. customafter recrystallisation from hexane the title compound (144.5 g)
  7. customis obtained in the form of a white crystalline solid

Sources & evidence

ORD record
ord-b4e8f8ab3a45410fa9733aab17459514
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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