Sodium Carbonate → 1-Bromo-2-[bis(4-fluorophenyl)methoxy]ethane

HRID 1032338Notes

Reaction equation

HRID 1032338 reaction equation
Br[CH:2]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:23][CH2:24][CH2:25][OH:26]>O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:26][CH2:25][CH2:24][Br:23])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 676651,1'-(Bromomethylene)bis(4-fluorobenzene)

Product 1

HCID 105681861-Bromo-2-[bis(4-fluorophenyl)methoxy]ethaneYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 49.5 g (0.175 mole) of bromo bis(4-fluoro phenyl)methane, 22.4 g (0.21 mole) of sodium carbonate and 26.9 g (0.21 mole) of 2-bromoethanol was stirred at 130° C. for 15 hours. After cooling, the reaction mixture was taken up with water and extracted with ether. The ethereal phase was washed, dried on sodium sulfate and then concentrated dry. Distillation of the residue yielded 41.9 g (yield: 69.4%) of 1-[bis(4-fluorophenyl) methoxy]-2-bromoethane.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washThe ethereal phase was washed
  4. customdried on sodium sulfate
  5. concentrationconcentrated
  6. customdry
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-cf0e627371b74d7bb7c0c58302ca1d8b
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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