Bromotrimethylsilane → 1-Bromomethyl-2-(3-methoxy-propoxy)-benzene

HRID 1809809Notes

Reaction equation

HRID 1809809 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11](C)[CH:10]=[CH:9][C:8]=1[CH2:14]O.C[Si](C)(C)[Br:18]>C(Cl)(Cl)Cl>[Br:18][CH2:14][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 67542816[2-(3-Methoxy-propoxy)-4-methyl-phenyl]-methanol

Product 1

HCID 593823491-Bromomethyl-2-(3-methoxy-propoxy)-benzeneYield 110.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the title C compound, [2-(3-methoxy-propoxy)-4-methyl-phenyl]-methanol (300 mg, 1.4 mmol) in 5 mL of chloroform is added trimethylbromosilane (0.28 mL, 2.1 mmol), with stiffing at room temperature. After 2 h the solvent is evaporated off and the crude residue is purified by flash column chromatography on silica gel (hexane/EtOAc 1/1) to afford the title compound as a colorless oil (0.4 g). Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 4.70 min.

Workup

  1. customwith stiffing at room temperature
  2. customAfter 2 h the solvent is evaporated off
  3. customthe crude residue is purified by flash column chromatography on silica gel (hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-ce9836561fc24128ae487e09217c6b82
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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