Bromoacetyl bromide → HCID 53823692, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([NH2:10])[CH:4]=1.C(=O)(O)[O-].[Na+].[Br:16][CH2:17][C:18](Br)=[O:19]>C(Cl)(Cl)Cl>[Br:16][CH2:17][C:18]([NH:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[OH:9])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-methoxy-2-aminophenol (3.0 g, 17.1 mmol) was dissolved in 100 mL of chloroform. 62 mL of saturated sodium bicarbonate solution was added and the new bi-phase mixture was stirred vigorously and cooled to 0° C. using an ice bath. Bromoacetylbromide (3.42 mL, 39 mmol) was added drop-wise. Fifteen minutes later the solution was removed from the ice bath and maintained at room temperature for 1.5 hours. HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) indicated that all of the starting material was gone and a new peak (Rt=4.9 min) had formed. The organic layer was separated and the aqueous phase was extracted with 100 mL of chloroform. The combined organic phases were dried over Na2SO4, filtered and concentrated to give 2-bromo-N-[2-hydroxy-5-(methyloxy)phenyl]acetamide (3.42 g, 13.1 mmol, 77%) as a brown amorphous solid. MS (ES) m/e 260 [M+H]+.
Workup
- customFifteen minutes later the solution was removed from the ice bath
- temperaturemaintained at room temperature for 1.5 hours
- customa new peak (Rt=4.9 min) had formed
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with 100 mL of chloroform
- dry with materialThe combined organic phases were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f30c2b14aef34b06b244f0d186beda19
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432258B2
Reaction notes
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