Sodium Hydroxide → 1-(Bromomethyl)-4-chloro-2-nitrobenzene

HRID 1982387Notes

Reaction equation

HRID 1982387 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.P(Br)(Br)[Br:14].[OH-].[Na+]>CCOCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Br:14])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 899564-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 105868161-(Bromomethyl)-4-chloro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 10 g of 4-chloro-2-nitrobenzyl alcohol in 200 mL of ether is added dropwise a solution of 17.7 g phosphorus tribromide in 100 mL of ether. The temperature of the reaction mixture is maintained at 15° or lower by means of cooling with an ice-water bath. On completion of the addition the reaction mixture is allowed to stir for an additional 1 hour at 15° and then at room temperature overnight. The reaction mixture is neutralized with 100 mL of 3N sodium hydroxide, and the layers are separated. The ethereal extracts are washed with 2×250 mL of brine, dried over anydrous sodium sulfate; the solvent is evaporated to dryness under reduced pressure to yield 4-chloro-2-nitrobenzyl bromide melting at 50°.

Workup

  1. temperatureThe temperature of the reaction mixture is maintained at 15° or lower by means
  2. temperatureof cooling with an ice-water bath
  3. additionOn completion of the addition the reaction mixture
  4. customat room temperature
  5. customovernight
  6. customthe layers are separated
  7. washThe ethereal extracts are washed with 2×250 mL of brine
  8. dry with materialdried over anydrous sodium sulfate
  9. customthe solvent is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8408fcf497ee45739ca636d2887ed467
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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