Chloromethyl Methyl Ether → 2-Bromo-4-chloro-1-(methoxymethoxy)benzene

HRID 2390314Notes

Reaction equation

HRID 2390314 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O:11][CH2:12]Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 696702-Bromo-4-chlorophenolHCID 81531Diisopropylethylamine

Product 1

HCID 107059212-Bromo-4-chloro-1-(methoxymethoxy)benzeneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-4-chlorophenol (3.00 g; 14.5 mmol) in DCM (20 ml) was treated with chloromethyl methyl ether (1.3 ml; 17 mmol) DIEA (3.3 ml; 19 mmol) for 18 hours. The solvents were evaporated, the residue was taken up in EtOAc, washed with sat. NH4Cl solution and brine, dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound as a colorless oil (3.27 g, 90%).

Workup

  1. customThe solvents were evaporated
  2. washwashed with sat. NH4Cl solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7eecd687d1cb4633802e6c460d26c5db
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…