Hydrochloric Acid → HCID 14954031, compound

HRID 2104435Notes

Reaction equation

HRID 2104435 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.II.Br[CH:13]([F:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>C1C=CC=CC=1.[Zn].C(OCC)(=O)C.O>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([F:19])[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:7])[CH3:18]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 77264-ChlorobenzaldehydeHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl ester

Product 1

HCID 14954031HCID 14954031, compoundYield 47.4%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Zinc powder (1.96 g) was added to 4-chlorobenzaldehyde (141 mg) dissolved in benzene (20 mL), and a catalytic amount of iodine was added to the mixture while refluxing by heating. Ethyl bromofluoroacetate (185 mg) in benzene (2.5 mL) was added dropwise thereto, followed by stirring for 2.5 hours. The reaction mixture was cooled by ice, 1N hydrochloric acid (12.5 mL) was added thereto, and the resultant mixture was stirred at room temperature for 1.5 hours. Water and ethyl acetate were added thereto for partiton. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure. The residue was purified by preparative thin layer chromatography (hexane:ethyl acetate=3:1), to thereby give the title compound (diastereomer mixture) (117 mg) as a colorless oil.

Workup

  1. temperaturewhile refluxing
  2. temperatureby heating
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customThe residue was purified by preparative thin layer chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-418d828fb06c498291d589477f77516c
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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