Water → HCID 67310078, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][NH2:8].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][C:20](Br)=[O:21].O>ClCCl>[Br:18][CH2:19][C:20]([NH:8][CH2:7][CH2:6][O:5][C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=1)=[O:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-(3-fluorophenoxy)ethylamine (0.93 g) and potassium carbonate (1.24 g in dichloromethane (20 mL) at 0° C. was treated with bromoacetyl bromide (1.04 mL). The reaction mixture was stirred at 0° C. for 30 mins then at room temperature for 6 h. Water was added and the mixture was stirred until effervescence ceased. The organic layer was separated and the organic layer was evaporated to afford the crude product which was purified by silica gel chromatography eluting with 0-50% EtOAc/pentane to give the sub-titled compound (1.17 g) as a brown oil.
Workup
- waitat room temperature for 6 h
- stirringthe mixture was stirred until effervescence
- customThe organic layer was separated
- customthe organic layer was evaporated
- customto afford the crude product which
- customwas purified by silica gel chromatography
- washeluting with 0-50% EtOAc/pentane
Sources & evidence
- ORD record
- ord-eef35d60839c43fa8cc3f38cf74ee82d
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329729B2
Reaction notes
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