Water → 2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

HRID 414998Notes

Reaction equation

HRID 414998 reaction equation
[H-].[Na+].O.[F:4][C:5]1[CH:6]=[C:7]([CH2:11][OH:12])[CH:8]=[CH:9][CH:10]=1.[Cl:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1F>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[O:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([F:4])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 680083-Fluorobenzylic alcohol

Product 1

HCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzeneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 1.4 g, 33.5 mmol) is suspended in dry DMF (10 ml) under a nitrogen atmosphere and the resulting mixture is cooled in ice:water. To above suspension is added dropwise over 15 minutes (3-Fluoro-phenyl)-methanol (2.90 ml, 27 mmol). Next, to the cold reaction mixture is added dropwise over 20 minutes a solution of 2-chloro-1-fluoro-4-nitro-benzene (4.2 g, 24 mmol) in dry DMF (20 ml). Upon the end of addition the cold bath is removed and the reaction mixture is stirred for another 4 hours. The reaction mixture is poured into 300 ml of ice:water. The resultant solid is isolated by suction filtration, washed with water (500 ml), and air dried to yield 5.5 g (20 mmol, 83%) of the clean desired material as an yellow powder.

Workup

  1. temperaturethe resulting mixture is cooled in ice
  2. customNext, to the cold reaction mixture
  3. additionUpon the end of addition the cold bath
  4. customis removed
  5. additionThe reaction mixture is poured into 300 ml of ice
  6. customThe resultant solid is isolated by suction filtration
  7. washwashed with water (500 ml), and air
  8. customdried

Sources & evidence

ORD record
ord-af2bfc3f80134cba9ea2a0d7d4ad50b2
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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