Boron tribromide → 5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

HRID 238706Notes

Reaction equation

HRID 238706 reaction equation
[NH2:1][C:2]1[C:3]([O:16]C)=[C:4]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)[Br:19]>ClCCl>[BrH:19].[NH2:1][C:2]1[C:3]([OH:16])=[C:4]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 574838045-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid

Product 1

HCID 574838055-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromideYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid 4f (2.79 g, 11.97 mmol) was dissolved in 25 mL of dichloromethane followed by dropwise addition of boron tribromide (23.9 mL, 2.0 M). The reaction mixture was reacted at room temperature for 1 hour. The mixture was concentrated under reduced pressure after 5 mL of methanol was added. The residue was diluted with 100 mL of ethyl acetate and stirred for 1 hour. Then the mixture was filtered and the filter cake was dried to obtain the title compound 5-(3-amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 4g (1.24 g, yield 47.2%) as a yellow solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure after 5 mL of methanol
  3. additionwas added
  4. additionThe residue was diluted with 100 mL of ethyl acetate
  5. filtrationThen the mixture was filtered
  6. customthe filter cake was dried

Sources & evidence

ORD record
ord-6f2ce8336a92476697488b8e81d3575d
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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