Benzyl Bromide → 1-Benzyloxy-2,3-difluoro-6-nitrobenzene

HRID 1188953Notes

Reaction equation

HRID 1188953 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([O:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 178588811-Benzyloxy-2,3-difluoro-6-nitrobenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-difluoro-6-nitrophenol (15.1 g), benzyl bromide (10.8 mL) and potassium carbonate (11.9 g) in N,N-dimethylformamide (60 mL) was stirred at room temperature for 15 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with successively water and brine, dried (MgSO4), filtered, and concentrated to give the title compound (22.1 g, 97%) as a light yellow solid. MS 264 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with successively water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41e1ae67a5af4afab211cac53676dbb3
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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