Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 86583515, compound

HRID 381823Notes

Reaction equation

HRID 381823 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)=[C:8]([F:18])[CH:7]=1.[C:19]([CH2:23][CH2:24][C:25](Cl)=[O:26])([O:21][CH3:22])=[O:20]>ClCCl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:25](=[O:26])[CH2:24][CH2:23][C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)=[C:8]([F:18])[CH:7]=1

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86583515HCID 86583515, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of anhydrous aluminum chloride (3.35 g, 0.0251 mol) in dichloromethane (30 mL) at 5° C. under nitrogen was added dropwise a solution of 4-bromo-2-fluoro-biphenyl (2.512 g, 0.0100 mol) in dichloromethane (17 mL) followed by a solution of 3-carbomethoxypropionyl chloride (1.34 mL, 0.0109 mol) in dichloromethane (16 mL), and the mixture stirred. After 2 hours at 5° C., the mixture was allowed to warm to room temperature and stirred for 20 hours. The reaction was recooled to 5° C. and quenched by the dropwise addition of water (60 mL). The organic layer was washed with water, saturated sodium bicarbonate, brine, and dried (Na2SO4). The organics were rotary evaporated, and the residue was purified by chromatography on silica gel, eluting with chloroform to give 3.15 g of 4-(4′-bromo-2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid; mp 94-95° C.

Workup

  1. stirringstirred for 20 hours
  2. customwas recooled to 5° C.
  3. customquenched by the dropwise addition of water (60 mL)
  4. washThe organic layer was washed with water, saturated sodium bicarbonate, brine
  5. dry with materialdried (Na2SO4)
  6. customthe residue was purified by chromatography on silica gel
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-277bfcae40604b94bd0588dcab189dbb
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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