Aluminum(III) Chloride → 7-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 2096603Notes

Reaction equation

HRID 2096603 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 58424408HCID 58424408, compound

Product 1

HCID 106815487-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-oneYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-(4-bromophenoxy)butanoyl chloride (27.6 g, 100 mmol) in DCM (200 mL) was added dropwise to a solution of AlCl3 (50 g, 0.38 mol) in DCM (100 mL) at 0° C. within 40 minutes, the mixture was stirred at 0° C. for 1.5 hours, and then stirred at room temperature overnight. the mixture was added to a stirred mixture of concentrated hydrochloric (500 mL) and ice, and then stirred for 1.5 hours. The mixture was extracted with DCM, washed with NaHCO3, dried over Na2SO4 and concentrated to give crude 7-bromo-3,4-dihydrobenz o[b]oxepin-5(2H)-one (25 g, 96%).

Workup

  1. stirringstirred at room temperature overnight
  2. additionthe mixture was added to a stirred mixture of concentrated hydrochloric (500 mL) and ice
  3. stirringstirred for 1.5 hours
  4. extractionThe mixture was extracted with DCM
  5. washwashed with NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ec1cd41412a4edc899f09a2146678b4
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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