Benzene → HCID 18314505, compound

HRID 1274574Notes

Reaction equation

HRID 1274574 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>ClC(Cl)C(Cl)Cl.Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chloride

Product 1

HCID 18314505HCID 18314505, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 65911,1,2,2-TetrachloroethaneSolvent

Conditions

Temperature
8 °C

Procedure

A solution of 2-chloro-4-fluoro-5-nitrobenzoyl chloride (26.7 g, 0.112 mol) and benzene (12.0 mL, 0.134 mol) in 1,1,2,2-tetrachloroethane is cooled to 0° C. to 5° C., treated with aluminum chloride (18.1 g, 0.136 mol), stirred for 15 minutes at about 8° C., heated to and stirred at 50° C. for one hour, cooled to room temperature, and diluted sequentially with an ice-water mixture and concentrated hydrochloric acid. The organic phase is separated, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Flash column chromatography of the solid using silica gel and methylene chloride gives the title product as an orange solid (30.8 g) which is identified by NMR spectral analyses.

Workup

  1. temperatureheated to and
  2. stirringstirred at 50° C. for one hour
  3. temperaturecooled to room temperature
  4. customThe organic phase is separated
  5. washwashed sequentially with water and saturated sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a solid

Sources & evidence

ORD record
ord-56719f2a02d44bf9a1671ed492afb9de
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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