Boron tribromide → 2,6-dihydroxy-N,N-dimethylbenzamide

HRID 488688Notes

Reaction equation

HRID 488688 reaction equation
C[O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[C:4]=1[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[OH:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:4]=1[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 32670112,6-dimethoxy-N,N-dimethylbenzamide

Product 1

HCID 222719252,6-dihydroxy-N,N-dimethylbenzamideYield 36.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,6-dimethoxy-N,N-dimethylbenzamide (64 mg, 0.3 mmol) dissolved in dichloromethane (2 mL) was added 1M BBr3 in dichloromethane (1 mL, 1.0 mmol)) under nitrogen atmosphere and stirred for 16 hours. The mixture was diluted with ethyl acetate and the mixture was washed with water (2×30 mL) and brine (2×30 mL). The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure to provide titled compound (20 mg). MS ESI(−)) m/e 180 (M−H)+; 1H NMR (300 MHz, DMSO-d6) 9.36 (s, 2H), 6.92 (t, 1H), 6.30 (d, 2H), 2.97-2.73 (m, 6H).

Workup

  1. washthe mixture was washed with water (2×30 mL) and brine (2×30 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-228c7495adcb4da885ff0176242fe696
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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