Methanol → 4-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

HRID 384352Notes

Reaction equation

HRID 384352 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])[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)[Br:19].CO>ClCCl>[BrH:19].[NH2:1][C:2]1[C:3]([OH:16])=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 574838254-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid

Product 1

HCID 574838264-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromideYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid 28d (325 mg, 1.4 mmol) was dissolved in 5 mL of dichloromethane followed by dropwise addition of boron tribromide (2.8 mL, 5.6 mmol). The mixture was reacted at room temperature for 4.5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. 5 mL of methanol was added and then the mixture was concentrated under reduced pressure. The residue was diluted with 10 mL of ethyl acetate and stirred for 0.5 hours. The mixture was filtered and the filter cake was dried to obtain the title compound 4-(3-amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 28e (174 mg, yield 57.1%) as a grey solid.

Workup

  1. customThe mixture was reacted at room temperature for 4.5 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with 10 mL of ethyl acetate
  4. filtrationThe mixture was filtered
  5. customthe filter cake was dried

Sources & evidence

ORD record
ord-a6090cf75ec145898344e9e4ffb8e387
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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