Benzyl bromoacetate → HCID 59333696, compound

HRID 1930730Notes

Reaction equation

HRID 1930730 reaction equation
CC(C)([O-])C.[Na+].[F:7][CH2:8][CH:9]([OH:12])[CH2:10][F:11].Br[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[F:7][CH2:8][CH:9]([O:12][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:10][F:11]

Participants

8

Reactant 4

HCID 62576Benzyl bromoacetateHCID 679851,3-Difluoro-2-propanolHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxide

Product 1

HCID 59333696HCID 59333696, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium tert-butoxide (0.923 g, 9.60 mmol) in DMF (20 mL)/THF (12 mL) mixture was cooled down to 0° C. and set under N2 atmosphere. 1,3-Difluoropropan-2-ol (0.717 mL, 9.25 mmol) was added via syringe and stirred for 40 min then benzyl 2-bromoacetate (1.373 mL, 8.73 mmol) was added dropwise via syringe and the mixture was stirred at rt for 16 hours. Ethyl acetate and sat NaHCO3 solution were added and the phases were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude oil was purified by silica gel chromatography (heptane/EtOAc gradient) to afford the title compound (0.91 g, 43% yield).

Workup

  1. stirringthe mixture was stirred at rt for 16 hours
  2. additionwere added
  3. customthe phases were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was purified by silica gel chromatography (heptane/EtOAc gradient)

Sources & evidence

ORD record
ord-424bc22195184185a097d1401d1bf97c
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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