Phosphorus tribromide → 4-(Bromomethyl)-3,5-difluorobenzonitrile

HRID 1627372Notes

Reaction equation

HRID 1627372 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH2:10]O)[C:5]#[N:6].P(Br)(Br)[Br:14]>C(Cl)Cl>[Br:14][CH2:10][C:9]1[C:2]([F:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[F:12]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 469414123,5-Difluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 667406914-(Bromomethyl)-3,5-difluorobenzonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-difluoro-4-(hydroxymethyl)benzonitrile (all material from above reaction) in DCM at 0° C. was added PBr3 (283 μL, 3 mmol). After stirring 1 h at 0° C., the reaction mixture was quenched with water and then extracted with DCM. The combined extracts were washed with satd NaHCO3, dried over Na2SO4 and concentrated to yield 4-(bromomethyl)-3,5-difluorobenzonitrile (0.88 g, 63%, combined yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.31-7.18 (m, 1H), 4.51 (d, J=10.1, 1H); GC-MS (ES) m/z 231 (M).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. washThe combined extracts were washed with satd NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-014f40635230441b9d3cc0720c733e2e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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