Chloromethyl Methyl Ether → HCID 90423535, compound

HRID 2272504Notes

Reaction equation

HRID 2272504 reaction equation
Cl[CH2:2][O:3][CH3:4].[Br:5][C:6]1[C:7]([F:13])=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:2][O:3][CH3:4])[C:7]=1[F:13]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 184012573-Bromo-2-fluorophenol

Product 1

HCID 90423535HCID 90423535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloro(methoxy)methane (11.8 mL) was added at 0 C to a THF (150 mL) solution of 3-bromo-2-fluorophenol (15.0 g) and N,N-diisopropylethylamine (41.1 mL). The reaction mixture was stirred overnight at room temperature in a nitrogen atmosphere and then filtered through celite. The obtained filtrate was washed with 1 M hydrochloric acid and a saturated aqueous solution of sodium bicarbonate in this order, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column (NH, hexane/ethyl acetate), and the solvent was distilled off under reduced pressure to obtain the title compound (17.9 g)

Workup

  1. filtrationfiltered through celite
  2. washThe obtained filtrate was washed with 1 M hydrochloric acid
  3. distillationa saturated aqueous solution of sodium bicarbonate in this order, and then, the solvent was distilled off under reduced pressure
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-854e09fe67fe4a69b872eb500c56c3f6
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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