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

HRID 1383930Notes

Reaction equation

HRID 1383930 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-4b186360e572450db20b64c0ae1b165e
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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