Chloromethyl Methyl Ether → 350672-95-6

HRID 1593071Notes

Reaction equation

HRID 1593071 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].Cl[CH2:15][O:16][CH3:17]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:15][O:16][CH3:17])[CH:7]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 99375-Fluoro-2-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 16085402350672-95-6

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-2-nitro-phenol (234 mg, 1.49 mmol) in 5 mL THF, sodium hydride (122 mg, 2.9 mmol) was added, followed by chloromethoxy methane (113 ul, 1.49 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 10 hours, then diluted with ethyl acetate and washed with brine. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-25% EtOAc/hexane) to give 4-fluoro-2-methoxymethoxy-1-nitro-benzene.

Workup

  1. washwashed with brine
  2. concentrationconcentrated in vacuo
  3. customto give a crude residue, which
  4. customwas purified by column chromatography (silica 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-642935e779634632ab0d956e307a76ad
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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