Boron tribromide → 2-Hydroxy-5-(pyridin-4-yl)benzaldehyde

HRID 2389661Notes

Reaction equation

HRID 2389661 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:7][C:4]=1[CH:5]=[O:6].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 105605352-Methoxy-5-(pyridin-4-yl)benzaldehyde

Product 1

HCID 1354483652-Hydroxy-5-(pyridin-4-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of aldehyde 192 (700 mg, 3.29 mmol) in DCM (8 mL) at −78° C. is treated with boron tribromide (0.93 mL, 9.85 mmol) dropwise over 5 minutes. After 1 h at −78° C., the reaction is warmed to RT and stirred 2 h. The reaction mixture is then cooled (0° C.), quenched with water (5 mL), basified with aqueous NaHCO3 (10 mL) and extracted into DCM (3×20 mL). The combined organic phases are dried over Na2SO4 and the solvent removed in vacuo to give the title compound.

Workup

  1. temperatureThe reaction mixture is then cooled (0° C.)
  2. customquenched with water (5 mL)
  3. extractionextracted into DCM (3×20 mL)
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7061ffd9b9444f2092539eabf78b991f
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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