Phosphorus tribromide → 4-(Bromomethyl)-2-chloro-3-methylbenzonitrile

HRID 15190

Reaction equation

HRID 15190 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([CH2:11]O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].P(Br)(Br)[Br:14]>C(Cl)Cl>[Br:14][CH2:11][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 685775712-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile

Product 1

HCID 685774134-(Bromomethyl)-2-chloro-3-methylbenzonitrileYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of compound 7B (700 mg, 3.9 mmol) in CH2Cl2 (15 mL) was added PBr3 (5.8 mL, 5.8 mmol, 1N in CH2Cl2) at −15° C., and stirred at −15° C. for 3 hr. The reaction was slowly quenched with saturated NaHCO3 solution at −15° C. The organic layer was separated, dried over MgSO4, and concentrated. Purification by silica gel chromatography (0-10% EtOAc in hexanes) provide the title compound (270 mg) as a white powder.

Workup

  1. customThe reaction was slowly quenched with saturated NaHCO3 solution at −15° C
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a53eda7a21c6493b8351a35a680eae0b
Source dataset
uspto-grants-2010_06
Patent number
US07732480B2

Linked notes

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