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

HRID 384386Notes

Reaction equation

HRID 384386 reaction equation
[NH2:1][C:2]1[C:3]([O:17]C)=[C:4]([C:9]2[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.B(Br)(Br)[Br:20]>ClCCl>[BrH:20].[NH2:1][C:2]1[C:3]([OH:17])=[C:4]([C:9]2[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 574838365-(3-Amino-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acid

Product 1

HCID 574838375-(3-Amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromideYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(3-Amino-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acid 46b (248 mg, 1 mmol) was dissolved in 20 mL of dichloromethane followed by dropwise addition of a solution of boron tribromide in dichloromethane (3 mL, 1 mmol/L). The reaction mixture was reacted at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure. The resulting residue was washed with ethyl acetate (50 mL×3) and dried to obtain the title compound 5-(3-amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromide 46c (172 mg, yield 54.7%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. washThe resulting residue was washed with ethyl acetate (50 mL×3)
  4. customdried

Sources & evidence

ORD record
ord-dc5fb015b817405ba46dc3b27b7b8d8a
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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