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

HRID 393591Notes

Reaction equation

HRID 393591 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1.[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=O)C.O>[CH2:13]([O:11][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([F:1])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluoro-2-methyl-5-nitrophenol (4.69 g, 27 mmol), benzyl bromide (3.59 ml, 30 mmol) and potassium carbonate (7.58 g, 55 mmol) in DMF (100 ml) was heated at 80° C. for 4 hours. The mixture was allowed to cool and diluted with water and stirred for 15 minutes. The precipitated product was collected by filtration, washed with water and dried to give 5-benzyloxy-2-fluoro-4-methyl-1-nitrobenzene (6.4 g, 89%).

Workup

  1. temperatureto cool
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1336121cb11649fcb06d01a7c426fdcc
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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