Hydrochloric Acid → 4-Bromo-4'-nitrobenzophenone

HRID 35988Notes

Reaction equation

HRID 35988 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 28256634-Bromo-4'-nitrobenzophenoneYield 85%

Conditions

Temperature
100 °C

Procedure

In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser were placed 4-nitrobenzoyl chloride (22.6 g, 0.122 mol), bromobenzene (100 g, 0.63 mol), and aluminum chloride (17.3 g, 0.13 mol). The mixture was heated for 3 h at 100° C., then cooled to room temperature and stirred for an additional 16 h. The mixture was poured into 1 L of acidic (HCl) ice water, and the organics were extracted using methylene chloride, dried over magnesium sulfate, and the solvents were removed under reduced pressure to yield a yellow powder. Recrystallization from acetone afforded 29.2 g (85% yield) of yellow crystals: m.p. 123°-124° C., (Lit. 122° C.). ##STR5##

Workup

  1. customIn a 250 mL flask equipped with a nitrogen inlet
  2. temperaturereflux condenser
  3. temperaturecooled to room temperature
  4. stirringstirred for an additional 16 h
  5. extractionthe organics were extracted
  6. dry with materialdried over magnesium sulfate
  7. customthe solvents were removed under reduced pressure
  8. customto yield a yellow powder
  9. customRecrystallization from acetone

Sources & evidence

ORD record
ord-6fe17835193343a7a4500ca2f185301b
Source dataset
uspto-grants-1995_05
Patent number
US05412066

Reaction notes

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