Phosphorus tribromide → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

HRID 2075069Notes

Reaction equation

HRID 2075069 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].P(Br)(Br)[Br:16]>ClCCl>[Br:16][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Product 1

HCID 116013693-(Bromomethyl)-5-(trifluoromethyl)benzonitrileYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-hydroxymethyl-5-trifluoromethyl-benzonitrile (100 mg, 0.497 mmol) in dichloromethane (1 ml) at 0° C. was treated in a dropwise manner with a solution of phosphorus tribromide (0.3 ml, 1M, 0.3 mmol) in dichloromethane at 0° C. for 1 hour. The ice bath was removed and the reaction was stirred at room temperature for 2 hours. Reaction was quenched with sat'd NaHCO3 solution until reaction was no longer yellow-orange in color. Reaction was extracted with dichloromethane and organic layer was dried over anhydrous magnesium sulphate and concentrated in vacuo. The crude residue was purified by chromatography on Biotage column (12+M), eluting with ethyl acetate in heptane 0-30% (10CV), 30% (2CV) to yield the title compound (56 mg, 43%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.46 (s, 2H) 7.80 (s, 1H) 7.84 (s, 2H).

Workup

  1. customThe ice bath was removed
  2. customReaction
  3. customwas quenched with sat'd NaHCO3 solution until reaction
  4. customReaction
  5. extractionwas extracted with dichloromethane and organic layer
  6. dry with materialwas dried over anhydrous magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by chromatography on Biotage column (12+M)
  9. washeluting with ethyl acetate in heptane 0-30% (10CV), 30% (2CV)

Sources & evidence

ORD record
ord-3e08b394b34741dcad2504dc961af4fd
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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