Hydrochloric Acid → HCID 22007973, compound

HRID 321893Notes

Reaction equation

HRID 321893 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.Cl.[CH2:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1)[CH2:18][CH3:19]>O1CCCC1>[F:15][C:11]1[CH:10]=[C:9]([C:27]([CH2:26][C:23]2[CH:24]=[CH:25][C:20]([CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=2)=[O:28])[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 140821-Bromo-3-fluorobenzeneHCID 13609014HCID 13609014, compound

Product 1

HCID 22007973HCID 22007973, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

In a mixture of 48.9 g (248.8 imol) of (4-propylphenyl)acetylchloride, 2.6 g (7.5 mmol) of tris(2,4-pentanedionata)iron (III), and 200 ml of toluene was added dropwise a solution of a Grignard reagent prepared from 56.6 g (323.5 mmol) of 1-bromo-3-fluorobenzene and 8.2 g (335.9 mmol) of Mg in 300 ml of tetrahydrofuran (THF) while maintaining them at a temperature lower than −60° C. After finishing of the dropping, they were stirred at the same temperature for 3 hours. Subsequently, the reaction mixture was raised up to room temperature, 200 ml of a diluted hydrochloric acid was added dropwise thereto, and then extracted with 150 ml of heptane. The organic layer thus obtained was washed with an aqueous sodium bicarbonate solution thrice and with water thrice, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under a reduced pressure, the residue was subjected to silica gel column chromatography (eluent: toluene/heptane=8/2) to obtain 43.3 g of a crude 3-fluoro-4′-propyldeoxybenzoin. This product was recrystallized from methanol to obtain 28.5 g of the subject compound. (Yield: 44.8%)

Workup

  1. additionwas added dropwise
  2. extractionextracted with 150 ml of heptane
  3. customThe organic layer thus obtained
  4. washwas washed with an aqueous sodium bicarbonate solution thrice and with water thrice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-dc8078d69dbc4434a2ff1900e45352b0
Source dataset
uspto-grants-2001_04
Patent number
US06210603B1

Reaction notes

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