Water → Benzene, 1-((2-(3,4-dichlorophenyl)-2-methylpropoxy)methyl)-3-(4-fluorophenoxy)-

HRID 1589444Notes

Reaction equation

HRID 1589444 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:7]=[CH:8][C:9]=1[Cl:10].[F:16][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH2:25]Br)=[CH:19][CH:18]=1.O>CN(C=O)C.C1(C)C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([O:21][C:20]3[CH:30]=[CH:31][C:17]([F:16])=[CH:18][CH:19]=3)[CH:23]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27374563-(4-Fluorophenoxy)benzyl BromideHCID 132166932-(3,4-Dichlorophenyl)-2-methylpropan-1-ol

Product 1

HCID 3067124Benzene, 1-((2-(3,4-dichlorophenyl)-2-methylpropoxy)methyl)-3-(4-fluorophenoxy)-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21735183Dimethylformamide tolueneSolvent

Procedure

To 20 ml of toluene was added 0.63 g of sodium hydride (60% in oil) and the mixture was refluxed, and a solution of 2.3 g of 2-(3,4-dichlorophenyl)-2-methylpropyl alcohol in 10 ml of 25% DMF/toluene was added dropwise to the mixture over a period of 15 minutes. The mixture was stirred for 15 minutes, and a solution of 3.5 g of 3-(4-fluorophenoxy)benzyl bromide in 10 ml of toluene was added dropwise to the mixture over a period of 20 minutes. Then, the mixture was refluxed for 1 hour and cooled to room temperature, and poured into water.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThen, the mixture was refluxed for 1 hour

Sources & evidence

ORD record
ord-9e739b8f3bd04d0a805a5e7ba4e44931
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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