Boron tribromide → HCID 57483856, compound

HRID 384408Notes

Reaction equation

HRID 384408 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]=2[O:17]C)=[CH:8][CH:9]=1)=[O:4].B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]=2[OH:17])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57483855HCID 57483855, compound

Product 1

HCID 57483856HCID 57483856, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(3-Amino-2-methoxy-phenyl)-furan-2-carboxylic acid methyl ester 54b (350 mg, 1.42 mmol) was dissolved in dichloromethane followed by dropwise addition of boron tribromide (3.3 mL, 2.0 mol/L). The reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials and quenched with methanol. The mixture was adjusted to pH 5˜6 with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layers were concentrated and then the resulting residue was purified by silica gel column chromatography to obtain the title compound 5-(3-amino-2-hydroxy-phenyl)-furan-2-carboxylic acid methyl ester 54c (170 mg, yield 45.1%) as a grey solid.

Workup

  1. customquenched with methanol
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layers were concentrated
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-64e32a66ebd24fd5bf804c75fe481f50
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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