Boron tribromide → HCID 18440061, compound

HRID 1896979Notes

Reaction equation

HRID 1896979 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#[N:12])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#[N:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2882193-methoxy-4-methylphenylacetonitrile

Product 1

HCID 18440061HCID 18440061, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-methoxy-4-methylphenylacetonitrile (2.0 g, 12.4 mmol) in dry CH2Cl2 (50 ml) cooled to −78° C., BBr3 1 M in CH2Cl2 (27 ml, 27 mmol) was added dropwise. The mixture was stirred overnight allowing the cooling bath to expire. The mixture was slowly poured in ice/water under stirring. When the ice melted, the aqueous phase was extracted with EtOAc and the organic phase was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude title compound (1.7 g, 93% yield) was used in the next step without further purification.

Workup

  1. stirringunder stirring
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6d83bc6d21e42d995154acadf859a6b
Source dataset
uspto-grants-2013_08
Patent number
US08519000B2

Reaction notes

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