Phosphorus tribromide → 1-(Bromomethyl)-2-chloro-4-nitrobenzene

HRID 629996Notes

Reaction equation

HRID 629996 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11]O.[Br:13]P(Br)Br>ClCCl>[Br:13][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1041472-Chloro-4-nitrobenzyl alcohol

Product 1

HCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-chloro-4-nitrophenyl)methanol (707 mg, 3.73 mmol) was dissolved in dichloromethane (15 mL) at 0° C. under nitrogen. Tribromophosphane (0.7 mL, 7.46 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by addition of 10% NaHCO3 solution (2 mL). After 10 minutes, Na2SO4 (15 g) was added. The solvent was filtered and evaporated to provide 1-(bromomethyl)-2-chloro-4-nitrobenzene, which was used without further purification.

Workup

  1. customThe reaction was quenched by addition of 10% NaHCO3 solution (2 mL)
  2. waitAfter 10 minutes
  3. additionNa2SO4 (15 g) was added
  4. filtrationThe solvent was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-bafae36aa8d94ddb813c935c3da52c38
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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