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

HRID 1667727Notes

Reaction equation

HRID 1667727 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzeneYield 96.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3.14 g (20 mmole) of 3-fluoro-4-nitro-phenol, 100 mL of acetonitrile and 8.3 g (60 mmole) of potassium carbonate was added 2.5 mL (21 mmole) of benzyl bromide. The mixture was heated to reflux for 1 hour, then cooled and concentrated under reduced pressure. The residue was stirred with 100 mL for 30 minutes. The solid was collected by filtration and air dried to give 4.76 g of 4-benzyloxy-2-fluoro-1-nitro-benzene as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe solid was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-762e32f5e2bf4205892689d251307d94
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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