Boron tribromide → 2-(2-Fluoro-4-hydroxyphenyl)-2-methylpropanenitrile

HRID 1453306Notes

Reaction equation

HRID 1453306 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10]([CH3:14])([CH3:13])[C:11]#[N:12].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]([CH3:14])([CH3:13])[C:11]#[N:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 450914982-(2-Fluoro-4-methoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 601250122-(2-Fluoro-4-hydroxyphenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-Fluoro-4-methoxy-phenyl)-2-methyl-propionitrile (1.5 g, 7.8 mmol) in CH2Cl2 (75 mL) at −78° C. was added Boron tribromide (1M solution in CH2Cl2) (16 mL, 16 mmol). The solution was allowed to warm to room temperature and stir for 48 hours. The reaction was quenched with 0.5N HCl (50 mL) and poured into water (100 mL). The organic layer was separated and the aqueous was extracted with CH2Cl2 (50 mL). The combined organics were washed with water (100 mL), dried over Na2SO4, filtered and concentrated. The resulting oil was used without further purification.

Workup

  1. customThe reaction was quenched with 0.5N HCl (50 mL)
  2. additionpoured into water (100 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous was extracted with CH2Cl2 (50 mL)
  5. washThe combined organics were washed with water (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting oil was used without further purification

Sources & evidence

ORD record
ord-7419275967ab428782b28ff006e0ba7a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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