4-Bromobenzoyl chloride → HCID 15029669, compound

HRID 1607276Notes

Reaction equation

HRID 1607276 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][C:16]1[C:20]2[C:21]([OH:29])=[C:22]([CH2:26][CH2:27][CH3:28])[CH:23]=[C:24]([Cl:25])[C:19]=2[O:18][CH:17]=1>C(Cl)CCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[O:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([CH2:26][CH2:27][CH3:28])=[C:21]([O:29][C:6](=[O:7])[C:5]4[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[C:20]=3[C:16]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14579737HCID 14579737, compound

Product 1

HCID 15029669HCID 15029669, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of p-bromobenzoyl chloride (1.1 gm; 5.0 mmoles) in ethylene dichloride (5 mL) was added slowly to a cooled suspension of aluminium chloride (3.3 gm; 25 mmoles) in ethylene dichloride (75 mL). After stirring for a period of 10 minutes, 3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (0.95 gm; 4.2 mmoles) in dichloroethylene (20 mL) was added over a period of 2 minutes. The reaction mixture was stirred at room temperature for 1 hour. It was cooled with an ice-bath and ice was added slowly. When the vigorous reaction subsided, the organic layer was separated and the aqueous phase was extracted with methylene chloride. The organic phases were combined, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 10% ethylacetate in hexane to yield 260 mg gm of 2-(p-bromobenzoyl-3-methyl-4-(p-bromobenzoyloxy)-5-propyl-7-chlorobenzofuran.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. temperatureIt was cooled with an ice-bath
  3. additionice was added slowly
  4. customWhen the vigorous reaction
  5. customthe organic layer was separated
  6. extractionthe aqueous phase was extracted with methylene chloride
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 10% ethylacetate in hexane

Sources & evidence

ORD record
ord-7a3e44f2e7124e3f891b2cd329a9fb4c
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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