Hydrochloric Acid → HCID 57445066, compound

HRID 558117Notes

Reaction equation

HRID 558117 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].Cl>C1COCC1.C(Cl)(Cl)Cl.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[C:12]([F:14])([F:13])[F:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 57445066HCID 57445066, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Charge 2-bromo-4-fluoro-benzaldehyde (6.1 g, 30.1 mmol) and trifluoromethyl trimethylsilane (5.4 g, 36.1 mmol) in THF (50 mL) in a 100-mL round bottom flask. Cool the solution to 0° C. under N2. Add Bu4NF (0.3 g, 1.20 mmol). Stir the mixture at 0° C. for another hour. Add hydrogen chloride (40 mL, 1 M, 40 mmol) to the mixture. Stir the mixture at RT overnight. Dilute the reaction mixture with chloroform. Wash the organic layer with water/aqueous saturated sodium chloride, dry over sodium sulfate, and concentrate in vacuo to give the crude product. Purify by FCC (hexanes/ethyl acetate, 4/1) to give the title compound as a yellow oil (7.40 g, 90%). MS (ES) m/z 273/275 [M+1]+.

Workup

  1. stirringStir the mixture at RT overnight
  2. washWash the organic layer with water/aqueous saturated sodium chloride
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customto give the crude product
  6. customPurify by FCC (hexanes/ethyl acetate, 4/1)

Sources & evidence

ORD record
ord-c6ff1b877bd14addad444fc37dc249b2
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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