Hydrochloric Acid → 4-Bromo-3'-nitrobenzophenone

HRID 35987

Reaction equation

HRID 35987 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([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:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:8])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 8495Benzoyl chloride, 3-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 123219594-Bromo-3'-nitrobenzophenoneYield 91.7%

Conditions

Temperature
100 °C

Procedure

In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser were placed 3-nitrobenzoyl chloride (28 g, 0.15 mol), bromobenzene (130 g, 0.83 mol), and aluminum chloride (22 g, 0.16 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 42.1 g (90% yield) of white crystals: m.p. 104°-105° C.

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-577526dbb11146de80d79d9d511240ce
Source dataset
uspto-grants-1995_05
Patent number
US05412066

Linked notes

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