2-(4-Fluorophenyl)acetic acid → 1,2-Bis(4-fluorophenyl)ethanone

HRID 2205119Notes

Reaction equation

HRID 2205119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O=S(Cl)Cl.C(Cl)Cl>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 98372-(4-Fluorophenyl)acetic acidHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27483631,2-Bis(4-fluorophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(4-fluorophenyl)acetic acid (5.0 g, 32.5 mmol, 1.00 equiv) in SOCl2 (30 mL) was heated for 3 hr at reflux in a 50-mL round-bottom flask. Most of SOCl2 was removed under vacuum, and the residue was added dropwise into a solution of AlCl3 (12.8 g, 96.2 mmol, 3.00 equiv) and fluorobenzene (6.1 g, 63.54 mmol, 2.00 equiv) in DCM (20 mL) at 0° C. The resulting solution was allowed to react, with stirring, for 2 hrs at room temperature.

Workup

  1. temperatureat reflux in a 50-mL round-bottom flask
  2. customMost of SOCl2 was removed under vacuum
  3. customto react

Sources & evidence

ORD record
ord-368cfb4a774449c7bdbfd0b14c4cbe59
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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