Boron tribromide → 4-(3-amino-2-hydroxy-phenyl)-1H-pyrrole-2-carboxylic acid

HRID 384419Notes

Reaction equation

HRID 384419 reaction equation
[NH2:1][C:2]1[C:3]([O:16]C)=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:3]([OH:16])=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 596156574-(3-amino-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 596156694-(3-amino-2-hydroxy-phenyl)-1H-pyrrole-2-carboxylic acidYield 114.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-amino-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 57h (130 mg, 0.56 mmol) in 2 mL of dichloromethane was added boron tribromide (1.12 mL, 2.24 mmol). The reaction mixture was stirred at room temperature for 6 hours. The reaction was monitored by TLC until the disappearance of the starting materials and quenched with methanol. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 4-(3-amino-2-hydroxy-phenyl)-1H-pyrrole-2-carboxylic acid 57i (140 mg, yield 99%) as a grey solid.

Workup

  1. customquenched with methanol
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9d2ec0722b9248fb9bb65a01be6d91e0
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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