tert-Butyl bromoacetate → tert-Butyl [2,2,2-Trifluoro-1-trifluoromethyl-1-(4-vinylphenyl)ethoxy]acetate

HRID 1007060Notes

Reaction equation

HRID 1007060 reaction equation
CC([O-])(C)C.[K+].[F:7][C:8]([F:24])([F:23])[C:9]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH2:22])=[CH:17][CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C1COCC1>[F:7][C:8]([F:23])([F:24])[C:9]([C:10]([F:12])([F:11])[F:13])([C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH2:22])=[CH:17][CH:16]=1)[O:14][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 27823772-(4-Ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 86586298tert-Butyl [2,2,2-Trifluoro-1-trifluoromethyl-1-(4-vinylphenyl)ethoxy]acetateYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of t-BuOK in THF (25.00 mL, 25.00 mmol) was slowly added to a solution of 1,1,1,3,3,3-Hexafluoro-2-(4-vinylphenyl)-2-propanol (5.48 g, 20.30 mmol) in THF (25 mL). The reaction mixture was allowed to stir at room temperature for 30 min, then cooled to −78° C. using a dry ice /acetone bath followed by the addition of t-butyl bromoacetate (3.75 mL, 25.40 mmol). The reaction mixture was allowed to slowly warm to room temperature overnight, concentrated, diluted with hexane, filtered through celite, and concentrated to provide 7.96 g of a reddish-yellow oil. This material was purified by column chromatography on silica gel using 50:1 hexane/ethyl acetate to provide 6.44 g (82%) of a colorless oil; 1H NMR (CDCl3) δ 7.60 (d, 2ArH), 7.50 (d, 2ArH), 6.75 (dd, CH═), 5.85 (dd, ═CHH), 5.40 (dd, ═CHH), 4.05 (s, CH2), 1.50 (s, t-Bu).

Workup

  1. temperaturecooled to −78° C.
  2. temperatureto slowly warm to room temperature overnight
  3. concentrationconcentrated
  4. additiondiluted with hexane
  5. filtrationfiltered through celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-904c7e17f93d426d89859ca3dcb2dfa3
Source dataset
uspto-grants-2004_09
Patent number
US06794109B2

Reaction notes

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