(3-Bromopropyl)benzene → 4-(3-bromopropyl)benzoyl Chloride

HRID 346248Notes

Reaction equation

HRID 346248 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)(=O)[C:12]([Cl:14])=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClC=C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:12]([Cl:14])=[O:13])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 113690154-(3-bromopropyl)benzoyl ChlorideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent

Procedure

To a cold (ice bath) stirred solution of 50.0 g (0.25 mole) of 1-bromo-3-phenylpropane (Aldrich) and 31.9 g (0.25 mole) of oxalyl chloride in 300 mL of trichloroethylene was added, portionwise, 33.3 g (0.25 mole) of aluminum chloride. The reaction mixture was stirred for 0.5 hr and then poured into ice water. The layers were separated and the aqueous layer was extracted with three 100 mL portions of methylene chloride. The combined organic layers were washed twice with 200 mL portions of water and dried (magnesium sulfate). The solvents were evaporated under reduced pressure to leave 63.6 g (97%) of 4-(3-bromopropyl)benzoyl chloride as an oil. To a solution of the acid chloride in 120 mL of dry benzene was added 60 mL of absolute ethanol and the mixture was heated at reflux for 3 hr. The solvents were evaporated under reduced pressure to give 63.4 g (93.5%) of an oil. The oil was purified by chromatography (3.5×90 cm glass column, 200 g of silica gel, benzene-hexane, 1:1). Fractions containing the desired component were combined and the solvents evaporated under reduced pressure to give 60.6 g (89%) of the title compound as a pale yellow oil.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with three 100 mL portions of methylene chloride
  4. washThe combined organic layers were washed twice with 200 mL portions of water
  5. dry with materialdried (magnesium sulfate)
  6. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-7656ab29036248cd9fcb524e8e91563d
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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