Boron tribromide → (4-Hydroxyphenyl)-2-pyridinylmethanone

HRID 473622Notes

Reaction equation

HRID 473622 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 80559(4-Methoxyphenyl)-2-pyridinylmethanone

Product 1

HCID 36317(4-Hydroxyphenyl)-2-pyridinylmethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-Methoxy-phenyl)-pyridin-2-yl-methanone (10.0 g, 0.046 mol) in DCM(140 mL) was added boron tribromide (17.8 mL, 0.187 mol) at −78° C. slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 h. Reaction mixture was quenched with saturated Sodium bicarbonate solution (250 mL) and extracted with ethyl acetate (2×250 mL). The organic layer was dried over sodium sulphate and concentrated. Purification by 100-200-mesh sized silica gel column with 0-40% EtOAc:Hexane as eluent provided the product.

Workup

  1. customReaction mixture
  2. customwas quenched with saturated Sodium bicarbonate solution (250 mL)
  3. extractionextracted with ethyl acetate (2×250 mL)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated
  6. customPurification by 100-200-mesh sized silica gel column with 0-40% EtOAc
  7. customHexane as eluent provided the product

Sources & evidence

ORD record
ord-4e2b8e9ac9aa4f6cb4c606937287e0c8
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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