Sodium hydride → HCID 22010447, compound

HRID 322966Notes

Reaction equation

HRID 322966 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].Br[CH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[O:8][CH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 22010447HCID 22010447, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-hydroxynitrobenzene (3 g) is added portionwise to a stirred suspension of sodium hydride (0.9 g, 60% dispersion in mineral oil) in dry dimethylformamide (50 mL) under nitrogen. After stirring for 20 minutes methyl 3-bromomethylbenzoate is added in one portion and stirring continued for 3 hours. The reaction mixture is evaporated to dryness and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase is washed three times with water (50 mL),dried over magnesium sulphate and evaporated to give a yellow solid which is crystallised from a mixture of ethyl acetate and cyclohexane (1:3 v/v) to give methyl 3-(3-fluoro-4-nitrophenoxymethyl]benzoate (4.95 g) as a white solid.

Workup

  1. additionis added in one portion
  2. customThe reaction mixture is evaporated to dryness
  3. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. washThe organic phase is washed three times with water (50 mL)
  5. customover magnesium sulphate and evaporated
  6. customto give a yellow solid which
  7. customis crystallised from a mixture of ethyl acetate and cyclohexane (1:3 v/v)

Sources & evidence

ORD record
ord-eb065cbef10b4c819819259bdd60db95
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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