Water → Benzene, 1-(4-bromophenoxy)-3-((2-(4-fluorophenyl)-2-methylbutoxy)methyl)-

HRID 1589448Notes

Reaction equation

HRID 1589448 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:15])([CH2:13][CH3:14])[CH2:11][OH:12])=[CH:6][CH:5]=1.[Br: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>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH2:13][CH3:14])([CH3:15])[CH2:11][O:12][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([O:21][C:20]3[CH:30]=[CH:31][C:17]([Br:16])=[CH:18][CH:19]=3)[CH:23]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 145170553-(4-Bromophenoxy)benzyl bromideHCID 155826502-(4-Fluorophenyl)-2-methylbutyl alcohol

Product 1

HCID 3067123Benzene, 1-(4-bromophenoxy)-3-((2-(4-fluorophenyl)-2-methylbutoxy)methyl)-Yield 76%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21735183Dimethylformamide tolueneSolvent

Procedure

To 20 ml of toluene was added 0.60 g of sodium hydride (60% in oil) and the mixture was refluxed, and a solution of 2.0 g of 2-(4-fluorophenyl)-2-methylbutyl alcohol in 10 ml of 40% DMF/toluene was added dropwise to the mixture over a period of 20 minutes. The mixture was stirred for 10 minutes and a solution of 4.0 g of 3-(4-bromophenoxy)benzyl bromide in 10 ml of toluene was added dropwise to the mixture over a period of 10 minutes. The mixture was further heated and refluxed for 1 hour and cooled to room temperature, and poured into water. The toluene layer was separated, washed with water, dried over Na2SO4, and evaporated under reduced pressure and the obtained crude ether was purified by column chromatography on 100 g of silica gel (1:1 mixed solvent of toluene and hexane was used as eluent) to give 3.7 g of the desired ether (the yield was 76% of the theoretical yield).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThe mixture was further heated
  3. temperaturerefluxed for 1 hour
  4. customThe toluene layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. customthe obtained crude ether
  9. customwas purified by column chromatography on 100 g of silica gel (1:1 mixed solvent of toluene and hexane was used as eluent)
  10. customto give 3.7 g of the desired ether (the yield was 76% of the
  11. customtheoretical yield)

Sources & evidence

ORD record
ord-7da913982da84d059818e40e8f6641d8
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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