Chloroacetyl chloride → 2-Chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone

HRID 2371890Notes

Reaction equation

HRID 2371890 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].COC(/C=C/[C:16]1[CH:21]=[C:20](O)[C:19]2[O:23][CH:24](C3C=CC(O)=C(O)C=3)[CH:25](C(OC)=O)[C:18]=2[CH:17]=1)=O>C(Cl)Cl>[Cl:1][CH2:2][C:3]([C:16]1[CH:21]=[CH:20][C:19]2[O:23][CH2:24][CH2:25][C:18]=2[CH:17]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 5857314DihydrobezofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 65041702-Chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Chloroacetyl chloride (10.39 g) was dissolved in methylene chloride (25 ml) and the solution was added to a slurry of aluminium chloride (12.2 g) in methylene chloride (50 ml) at -15° C. A solution of dihydrobenzofuran (10 g) in methylene chloride (25 ml) was added and the solution was allowed to warm to room temperature over 20 hours. The reaction mixture was poured into ice (700 g) and the aqueous layer was back-washed with methylene chloride (2×200 ml). The combined organic extracts were washed with water (800 ml), dried with MgSO4 and concentrated in vacuo. The resulting solid (11 g) was heated in cyclohexane (110 ml) and the supernatant liquid decanted off and allowed to crystallise. Filtration produced the title compound as a white solid, yield 2.1 g, m.p. 85°-87° C.

Workup

  1. washthe aqueous layer was back-washed with methylene chloride (2×200 ml)
  2. washThe combined organic extracts were washed with water (800 ml)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. temperatureThe resulting solid (11 g) was heated in cyclohexane (110 ml)
  6. customthe supernatant liquid decanted off
  7. customto crystallise
  8. filtrationFiltration

Sources & evidence

ORD record
ord-ab49e25b747249d59885675ade2e448b
Source dataset
uspto-grants-1992_03
Patent number
US05096890

Reaction notes

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