Sodium Hydroxide → HCID 14517065, compound

HRID 1904979Notes

Reaction equation

HRID 1904979 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:26]([F:29])([F:28])[F:27])[CH2:24][OH:25])=[CH:19][CH:18]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][O:25][CH2:24][CH:23]([C:20]1[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][CH:21]=1)[C:26]([F:27])([F:28])[F:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 14517052HCID 14517052, compound

Product 1

HCID 14517065HCID 14517065, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 12.58 g of 3-phenoxybenzyl bromide and 10.74 g of 2-(4-chlorophenyl)3,3,3-trifluoropropanol in 30 ml of toluene was slowly added to the mixture of 1.00 g of benzyltriethylammonium chloride, 12.76 g of 45% aqueous sodium hydroxide solution and 15 ml of toluene with ice-cooling. The reaction solution was stirred at room temperature for 14 hours. Thereafter, the reaction solution was poured into dilute hydrochloric acid-ice water and extracted with toluene. The toluene layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure, and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/toluene (2:1) mixture] to obtain 16.06 g of the desired compound.

Workup

  1. temperaturecooling
  2. extractionextracted with toluene
  3. washThe toluene layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-b9803c5151a54b76a2f0bcd2a56a222a
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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