1,2-Dibromoethane → [2-[4-(3,3-Dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]bromide

HRID 1700912Notes

Reaction equation

HRID 1700912 reaction equation
[CH3:1][O:2][C:3]([O:17][CH3:18])([C:13]([F:16])([F:15])[F:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27]Br>>[CH3:18][O:17][C:3]([O:2][CH3:1])([C:13]([F:15])([F:16])[F:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:27][CH2:26][Br:25])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 183189964-(3,3-Dimethoxy-4,4,4-trifluorobut-1-yl)phenol

Product 1

HCID 18319078[2-[4-(3,3-Dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]bromideYield 86.9%

Conditions

Temperature
130 °C

Procedure

A mixture of 4-(3,3-dimethoxy-4,4,4-trifluorobut-1-yl)phenol (1.64 g, 6.2 mmol), potassium carbonate (1.3 g, 9.3 mmol) and 1,2-dibromoethane (5 ml, 58 mmol) was stirred and heated under reflux (130° C.) for 26 h. After cooling to room temperature, the mixture was filtered and washed with ethyl actate. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate 20:1 to 4:1) to give the title compound (2.0 g, 85%) as a colorless liquid.

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. washwashed with ethyl actate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate 20:1 to 4:1)

Sources & evidence

ORD record
ord-b2342d83240740e78d8429d622f1d9e6
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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