Hydrochloric Acid → 1-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanone

HRID 2101230Notes

Reaction equation

HRID 2101230 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[C:27](Cl)(=[O:29])[CH3:28].Cl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:27](=[O:29])[CH3:28])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7416NitrobenzeneHCID 94614-FluorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6081141-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4′-Fluoro-biphenyl (0.03 mol) was added to 1 M AlCl3 in nitrobenzene (40 mL, 0.04 mol) with chilling in an ice bath. Acetyl chloride (0.06 mol) was added dropwise and the mixture stirred overnight at room temperature. The dark solution was poured into a mixture of crushed ice (150 mL), water (25 mL) and HCl (50 mL). The aqueous phase was separated and the nitrobenzene removed by steam distillation to give a dark low melting solid. The solid was recrystallised from aqueous methanol to give the title compound. δC (CDCl3, 62.9 MHz): 26.7, 115.9 (d, J 21.5), 127.1, 129.0 (d, J=7.8), 135.8, 136.0 (d, J 2.9), 144.7, 163.0 (d, J 248.0) and 197.8.

Workup

  1. temperaturewith chilling in an ice bath
  2. customThe aqueous phase was separated
  3. customthe nitrobenzene removed by steam distillation
  4. customto give a dark low melting solid
  5. customThe solid was recrystallised from aqueous methanol

Sources & evidence

ORD record
ord-4e8acfa88412423aa97d6545f9d00741
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

Loading…