Benzyl Bromide → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 1593072Notes

Reaction equation

HRID 1593072 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.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N.C(OCC)(=O)C>[CH2:12]([O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 10796Cesium carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-fluoro-2-nitro-phenol (464 mg, 2.95 mmol), benzyl bromide (0.37 ml, 3.10 mmol) and cesium carbonate (1.055 g, 3.24 mmol) in MeCN (10 mL) was stirred room temperature under argon for 48 hours. The reaction mixture was 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 2-benzyloxy-4-fluoro-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-0f00944ef9194a7694c17afbe89eb51b
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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