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

HRID 238721Notes

Reaction equation

HRID 238721 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 22d (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. 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 22e (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-c2593e4ffe9249e797b5125041a23a2d
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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