Benzyl Bromide → 5-Benzyloxy-2-fluoro-4-methylnitrobenzene

HRID 1057350Notes

Reaction equation

HRID 1057350 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([O:17][C:13]1[C:14]([CH3:16])=[CH:15][C:10]([F:9])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 108210594-Fluoro-2-methyl-5-nitrophenol

Product 1

HCID 219910575-Benzyloxy-2-fluoro-4-methylnitrobenzeneYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The starting material 5-benzyloxy-2-fluoro-4-methylnitrobenzene was obtained by adding benzyl bromide (3 ml, 25 mmol) to a solution of 2-fluoro-5-hydroxy-4-methylnitrobenzene (3.92 mg, 23 mmol) in DMF (70 ml) containing potassium carbonate (9.5 g, 68 mmol). After stirring for 3 hours at 60° C., the mixture was diluted with water and adjusted to pH2. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The solid was filtered off, washed with hexane and dried under vacuum to give 5-benzyloxy-2-fluoro-4-methylnitrobenzene (4.83 g, 80%).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialbrine, dried (MgSO4)
  4. customthe solvent evaporated
  5. filtrationThe solid was filtered off
  6. washwashed with hexane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-366e6e684c544a08bf8344d4e24ece50
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

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