2-Bromophenol → 1-Bromo-2-(methoxymethoxy)benzene

HRID 1289179Notes

Reaction equation

HRID 1289179 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20]Cl>>[CH3:18][O:19][CH2:20][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

4

Reactant 3

HCID 72442-BromophenolHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 113104791-Bromo-2-(methoxymethoxy)benzeneYield 58%

Procedure

To a solution of 2-bromophenol (0.67 ml, 5.8 mmol) and diisopropylethylamine (1.1 ml, 6.4 mmol) was added chloromethyl methyl ether (0.49 ml, 6.4 mmol). The reaction mixture was stirred at ambient temperature for 2 h, quenched with sat'd NaHCO3 and diluted with CH2Cl2. The organic phase was washed with water and dried over Na2SO4 to afford 700 mg (58%) of the title compound.

Workup

  1. customquenched with sat'd NaHCO3
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e9954c40a5e740afbe39b891f8c8c7d3
Source dataset
uspto-grants-1998_05
Patent number
US05747540

Reaction notes

Loading…