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

HRID 2359652Notes

Reaction equation

HRID 2359652 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-8f6ddefddd9d4b28be06b67330f8264e
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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