Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 86583516, compound

HRID 381828Notes

Reaction equation

HRID 381828 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl: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>[Cl: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 6451240Aluminum(III) ChlorideHCID 183641304-Chloro-2-fluoro-1,1'-biphenyl

Product 1

HCID 86583516HCID 86583516, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of anhydrous aluminum chloride (1.451 g, 0.0109 mol) in dichloromethane (20 mL) under nitrogen at 5° C. was added dropwise a solution of 4-chloro-2-fluorobiphenyl (0.858 g, 0.00415 mol) in dichloromethane (13 mL) over 10 minutes followed by the dropwise addition of 3-carbomethoxypropionyl chloride (0.57 mL, 0.0046 mol) in dichloromethane (13 mL) over 25 minutes. The resulting mixture was stirred for 2.5 hours then allowed to warm slowly to room temperature. Stirred for 3 days, for convenience. Then the mixture was recooled and quenched with the dropwise addition of water (145 mL). The organic layer was washed with water, aqueous sodium bicarbonate, brine, and dried (MgSO4). The mixture was rotary evaporated to give 1.25 g of 4-(4′-chloro-2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid: mp 90.5-92.5° C.

Workup

  1. stirringStirred for 3 days, for convenience
  2. customquenched with the dropwise addition of water (145 mL)
  3. washThe organic layer was washed with water, aqueous sodium bicarbonate, brine
  4. dry with materialdried (MgSO4)
  5. customThe mixture was rotary evaporated

Sources & evidence

ORD record
ord-c3219411084b4c9fb6c86d842b8cd3d9
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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