Boron tribromide → HCID 66746738, compound

HRID 331681Notes

Reaction equation

HRID 331681 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]#[N:12].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:10]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:11]#[N:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66747923HCID 66747923, compound

Product 1

HCID 66746738HCID 66746738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred and cooled (0° C.) solution of 2-(2-fluoro-5-methoxy-phenyl)-3-phenyl-propionitrile (5.68 g, 22.25 mmol) in 150 ml dichloromethane under argon was added dropwise a 1M solution of boron tribromide in dichloromethane (66.7 ml, 66.7 mmol). The reaction was allowed to warm up to room temperature. The mixture was stirred over night, poured on ice water, diluted with dichloromethane. The organic layer was separated and the aqueous layer extracted twice with dichloromethane. The combined organic layers were washed subsequently with water, saturated sodium bicarbonate solution and brine, then dried over sodium sulphate and filtered. Evaporation of solvent afforded a pale brown solid.

Workup

  1. stirringThe mixture was stirred over night
  2. additionpoured on ice water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted twice with dichloromethane
  5. washThe combined organic layers were washed subsequently with water, saturated sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customEvaporation of solvent
  9. customafforded a pale brown solid

Sources & evidence

ORD record
ord-ce45d21657fa407c941cceebfc1c6d46
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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