1,4-Benzodioxan → Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-

HRID 1022463Notes

Reaction equation

HRID 1022463 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[O:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH2:13]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([C:20]1[CH:19]=[CH:18][C:17]2[O:12][CH2:13][CH2:14][O:15][C:16]=2[CH:21]=1)=[O:5]

Participants

5

Reactant 3

HCID 103011,4-BenzodioxanHCID 6451240Aluminum(III) ChlorideHCID 583408092-Bromo-5-iodobenzoyl chloride

Product 1

HCID 58340798Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-Yield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-5-iodo-benzoyl chloride (−158 g, 457 mmol) in DCM (1500 ml) was added benzo(1,4)-dioxane (65.8 ml, 549 mmol) at 0° C. To this reaction mixture, aluminum chloride (195.4 g, 1465 mmol) was added in portions. After stirring for overnight at room temperature, reaction mixture was poured into crushed ice. This was extracted with dichloromethane (1000 ml×2). Dichloromethane layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate solution (1000 ml×2), brine (1000 ml), dried over sodium sulfate, and concentrated. The solid product was triturated with hexanes. The product was dried under vacuum to give 180 g of (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone.

Workup

  1. customreaction mixture
  2. additionwas poured
  3. custominto crushed ice
  4. extractionThis was extracted with dichloromethane (1000 ml×2)
  5. washDichloromethane layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate solution (1000 ml×2), brine (1000 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe solid product was triturated with hexanes
  9. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-ef8c683df2d84731829d59d691fc2805
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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