4-Bromobiphenyl → HCID 15541117, compound

HRID 381816Notes

Reaction equation

HRID 381816 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:18]([CH2:22][CH2:23][C:24](Cl)=[O:25])([O:20][CH3:21])=[O:19]>ClCCl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:24](=[O:25])[CH2:23][CH2:22][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 71014-BromobiphenylHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15541117HCID 15541117, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of anhydrous aluminum chloride (3.45 g, 0.026 mol) in dichloromethane (20 mL) at 5° C. was added dropwise a solution of 4-bromobiphenyl (2.3 g, 0.010 mol) in dichloromethane (11 mL) followed by the dropwise addition of 3-carbomethoxypropionyl chloride (1.35 mL, 0.011 mol) in dichloromethane (15 mL), and the mixture stirred. After 2 hours at 5° C., the mixture was allowed to warm to room temperature. After 1 day, the reaction was cooled to 5° C. and quenched by the dropwise addition of water (50 mL). The layers were separated, and the organic layer washed with water and brine, dried (MgSO4), and rotary evaporated. The residue was dissolved (CH2Cl2) and purified by column chromatography on silica gel, eluting with dichloromethane to give 2.68 g of 4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 115.0-116.5° C.

Workup

  1. waitAfter 1 day
  2. temperaturethe reaction was cooled to 5° C.
  3. customquenched by the dropwise addition of water (50 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with water and brine
  6. dry with materialdried (MgSO4), and rotary evaporated
  7. dissolutionThe residue was dissolved (CH2Cl2)
  8. custompurified by column chromatography on silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-81286068ecd2459c9b0f5f1054bb056f
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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