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

HRID 634674Notes

Reaction equation

HRID 634674 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), (prepared as described for the starting material in Example 8), 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 reaction 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. custom(prepared
  2. temperatureto cool
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6e5a4962ee24415794fc0b3f5d8e1bf0
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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