Phosphorus tribromide → 4-(Bromomethyl)-2,5-difluorobenzonitrile

HRID 508431Notes

Reaction equation

HRID 508431 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10]O)[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5].P(Br)(Br)[Br:14]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][Br:14])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 219046532,5-Difluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 534042034-(Bromomethyl)-2,5-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2,5-difluoro-4-(hydroxymethyl)benzonitrile (Preparation 21, 390 mg, 2.30 mmol) in DCM (12 mL) was added phosphorus tribromide (0.238 mL, 2.53 mmol). The mixture was stirred at room temperature for 18 hours. The reaction mixture was then diluted with DCM to 30 mL and washed with saturated aqueous sodium bicarbonate (30 mL). The organic layer was dried over sodium sulphate, and evaporated to afford the title compound as a yellow oil, which was used in the next step without further purification (530 mg, 99%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (30 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-7bf587651a9b4fe39c122338c0e6831d
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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