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

HRID 642749

Reaction equation

HRID 642749 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-methylbenzonitrile

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.

Workup

  1. customThe reaction was slowly quenched with saturated NaHCO3 solution at −15° C.

Sources & evidence

ORD record
ord-a46c7acaaea94ee58f98a39797973cdf
Source dataset
uspto-grants-2010_04
Patent number
US07696241B2

Linked notes

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