2-Fluorobiphenyl → 4-(2'-Fluoro-biphenyl-4-yl)-4-oxo-butyric acid methyl ester

HRID 1979150Notes

Reaction equation

HRID 1979150 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([CH2:18][CH2:19][C:20](Cl)=[O:21])([O:16][CH3:17])=[O:15].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:17][O:16][C:14](=[O:15])[CH2:18][CH2:19][C:20]([C:11]1[CH:10]=[CH:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:13][CH:12]=1)=[O:21]

Participants

5

Reactant 3

HCID 675792-FluorobiphenylHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 214918674-(2'-Fluoro-biphenyl-4-yl)-4-oxo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to Example 2, Step (a), 2-fluoro-biphenyl (6.284 g, 0.0365 mol) was allowed to react with 3-carbomethoxypropionyl chloride (4.95 mL, 0.0402 mol) in the presence of anhydrous aluminum chloride (10.7 g, 0.0802 mol) in dichloromethane to give, after chromatography on silica gel (456 g, 230-400 mesh), eluting with chloroform (15×450 mL), 7.36 g of 4-(2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid; mp 75.5-77.5° C.

Workup

  1. customto give
  2. washafter chromatography on silica gel (456 g, 230-400 mesh), eluting with chloroform (15×450 mL), 7.36 g of 4-(2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a pale yellow solid

Sources & evidence

ORD record
ord-2ee11c0735144ad18ae16e6a8d0b0adf
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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