Boron tribromide → HCID 11638630, compound

HRID 19969Notes

Reaction equation

HRID 19969 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]3[O:22]C[O:24][C:18]=3[CH:17]=2)[CH:6]=[CH:7][C:8]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].B(Br)(Br)Br>CO>[OH:2][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:24])[CH:17]=2)[CH:6]=[CH:7][C:8]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 37259044N-(3-methoxy-4-methanesulfonylaminophenyl)-3,4-methylenedioxybenzamide

Product 1

HCID 11638630HCID 11638630, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of N-(3-methoxy-4-methanesulfonylaminophenyl)-3,4-methylenedioxybenzamide (200 mg) in dry CH3Cl2 (20 ml) under nitrogen, was added boron tribromide (0.3 ml) then stirring continued for a further 20 hours. Methanol (50 ml) was added carefully, then the solvent evaporated in vacuo to a volume of 1 ml, this was repeated 2 more times. Purification by column chromatography over silica gel eluting with chloroform containing methanol (10-20%) gave N-(3-hydroxy-4-methanesulfonylaminophenyl)-3,4-dihydroxybenzamide (62 mg, 33%) as pale brown crystals.

Workup

  1. customthe solvent evaporated in vacuo to a volume of 1 ml
  2. customPurification by column chromatography over silica gel eluting with chloroform
  3. additioncontaining methanol (10-20%)

Sources & evidence

ORD record
ord-bab2e04925e64859980f622da98ae4e7
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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