Hydrochloric Acid → HCID 67133700, compound

HRID 1295606Notes

Reaction equation

HRID 1295606 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].[CH:15](=[O:19])[CH:16]([CH3:18])[CH3:17].Cl>C(OCC)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH:15]([OH:19])[CH:16]([CH3:18])[CH3:17])=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 6561IsobutyraldehydeHCID 1361722-Bromo-5-chlorobenzotrifluoride

Product 1

HCID 67133700HCID 67133700, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard is prepared from 1.77 g (73 mmol) of iodine-activated magnesium and 18.70 g (72 mmol) 1-bromo-4-chloro-2-trifluoromethyl-benzene dissolved in 150 mL diethyl ether. 5.46 g (72 mmol) isobutyraldehyde in 30 mL diethyl ether are added dropwise to the Grignard reagent at ambient temperature. After the addition has ended the reaction mixture is refluxed for 30 minutes and then stirred overnight at ambient temperature. It is combined with ice water and acidified with hydrochloric acid. The aqueous phase is separated off and extracted with diethyl ether. The organic phases are combined, dried with sodium sulphate and evaporated down. The residue is chromatographed on a silica gel column (petroleum ether/ethyl acetate=9:1). 10.5 g of oil.

Workup

  1. additionAfter the addition
  2. temperatureis refluxed for 30 minutes
  3. customThe aqueous phase is separated off
  4. extractionextracted with diethyl ether
  5. dry with materialdried with sodium sulphate
  6. customevaporated down
  7. customThe residue is chromatographed on a silica gel column (petroleum ether/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-39b831b2ad3a4bbb9bfb2aebc10b0e6d
Source dataset
uspto-grants-2007_07
Patent number
US07244728B2

Reaction notes

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