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Water → HCID 67310078, compound

HRID 2192359
Notes
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Reaction equation

HRID 2192359 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 142453302-(3-Fluorophenoxy)ethan-1-amine

Product 1

HCID 67310078HCID 67310078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. waitat room temperature for 6 h
  2. stirringthe mixture was stirred until effervescence
  3. customThe organic layer was separated
  4. customthe organic layer was evaporated
  5. customto afford the crude product which
  6. customwas purified by silica gel chromatography
  7. washeluting with 0-50% EtOAc/pentane

Sources & evidence

ORD record
ord-eef35d60839c43fa8cc3f38cf74ee82d
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329729B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes