Acetyl chloride → HCID 66760945, compound

HRID 1850408Notes

Reaction equation

HRID 1850408 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1.[Br:12][C:13]1[C:14]([CH3:25])=[CH:15][C:16]2[O:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]=2[C:23]=1[CH3:24].[C:26](Cl)(=[O:28])[CH3:27]>C(OCC)(=O)C.O>[Br:12][C:13]1[C:14]([CH3:25])=[C:15]([C:26](=[O:28])[CH3:27])[C:16]2[O:20][C:19]([CH3:21])([CH3:22])[CH2:18][C:17]=2[C:23]=1[CH3:24]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 66759943HCID 66759943, compound

Product 1

HCID 66760945HCID 66760945, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Aluminium chloride (3.56 g, 26.7 mmol) was added to a mixture of chlorobenzene (40 mL) containing 5-bromo-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran (4.55 g, 17.8 mmol) synthesized in Reference Example 120 and acetyl chloride (4.20 g, 53.4 mmol) at −40° C., and the mixture was stirred at the same temperature. After stirring for 1 hour, the reaction solution was poured into water, and extraction was performed using ethyl acetate. The extract was washed with saturated sodium bicarbonate water and saturated saline, and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-95/5) to give 440 mg of the title compound (yield: 8%).

Workup

  1. stirringAfter stirring for 1 hour
  2. washThe extract was washed with saturated sodium bicarbonate water and saturated saline
  3. customdried
  4. customAfter that, the solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-95/5)

Sources & evidence

ORD record
ord-4147ac8bfc8f41cf9d999458964f8485
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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