Boron tribromide → N,N-Diethyl-3-hydroxybenzamide

HRID 1894165Notes

Reaction equation

HRID 1894165 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[CH:6]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 669438N,N-diethyl-3-methoxybenzamide

Product 1

HCID 13159769N,N-Diethyl-3-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 15a (0.68 g; 3.28 mmol) in CH2Cl2 (50 mL) was added BBr3 (1.0M in CH2Cl2) (16 mL; 16 mmol) dropwise at 0° C. The reaction was stirred at room temperature for 1 h. The mixture was quenched with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated to afford Compound 15b. The crude product was used in the next reaction without further purification. MS m/z 194.2 (M+H)+.

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e2d39c1d830c4dd68885677bb4c0d4b3
Source dataset
uspto-grants-2013_08
Patent number
US08513271B2

Reaction notes

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