Allyl bromide → Allyl (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ether

HRID 1071579Notes

Reaction equation

HRID 1071579 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C@H:13]([OH:15])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22]>O1CCCC1>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][CH2:22][CH:21]=[CH2:20])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 2779031(alphaR)-alpha-Methyl-3,5-bis(trifluoromethyl)benzenemethanol

Product 1

HCID 86591711Allyl (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethanol (5.00 g) in tetrahydrofuran (20 ml) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.16 g). After 30 minutes, allyl bromide (3.35 ml) was added and the mixture refluxed for 16 hours. The reaction was quenched by careful addition of saturated NH4Cl solution at 0° C. and diluted with diethyl ether. The organics were dried (brine, MgSO4) and concentrated under reduced pressure to afford the title compound as a crude oil.

Workup

  1. temperaturethe mixture refluxed for 16 hours
  2. customThe reaction was quenched by careful addition of saturated NH4Cl solution at 0° C.
  3. additiondiluted with diethyl ether
  4. dry with materialThe organics were dried (brine, MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-266aeba186674fa3a7cad0e5d67d85bd
Source dataset
uspto-grants-2005_06
Patent number
US06906085B2

Reaction notes

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