Boron tribromide → HCID 57483852, compound

HRID 384404Notes

Reaction equation

C[O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[O:14][C:13]([CH3:15])=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1.B(Br)(Br)[Br:20]>ClCCl>[BrH:20].[OH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[O:14][C:13]([CH3:15])=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(2-Methoxy-3-amino-phenyl)-2-methyl-furan-3-carboxylic acid 53d (370 mg, 1.5 mmol) was dissolved in dichloromethane. The mixture was cooled to 0° C. by an ice-water bath followed by dropwise addition of a solution of boron tribromide in dichloromethane (1 N, 3.6 mL). Upon completion of the addition, the reaction mixture was reacted at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials and quenched by addition of 0.5 mL of methanol. The mixture was stirred for 30 minutes and concentrated under reduced pressure. The resulting residue was diluted with 10 mL of ethyl acetate and stirred for 30 minutes. The mixture was filtered and the filter cake was dried to obtain the title compound 5-(2-hydroxy-3-amino-phenyl)-2-methyl-furan-3-carboxylic acid hydrobromide 53e (240 mg, yield 46%) as a grey solid.

Workup

additionUpon completion of the addition
customthe reaction mixture was reacted at room temperature for 2 hours
customquenched by addition of 0.5 mL of methanol
concentrationconcentrated under reduced pressure
additionThe resulting residue was diluted with 10 mL of ethyl acetate
stirringstirred for 30 minutes
filtrationThe mixture was filtered
customthe filter cake was dried

Sources & evidence

ORD record: ord-3ba194c182b948c89bc371c346485b1b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367710B2

Reaction notes

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