Bromobenzene → 4-Bromo-3'-nitrobenzophenone

HRID 640955Notes

Reaction equation

HRID 640955 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12])([O-:7])=[O:6].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:11]([C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=2)=[O:12])=[CH:20][CH:19]=1

Participants

5

Reactant 3

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

Product 1

HCID 123219594-Bromo-3'-nitrobenzophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 5 L, 3-necked round bottomed flask equipped with an overhead stirrer, dropping funnel, N2(g) inlet was charged with AlCl3 (432.5 g, 3.24 mol). The solids were cooled to 0° C. with an ice-H2O bath. DMF (71 ml) was added dropwise over a period of 35 min and the temperature was kept under 32° C. during the addition. The reaction mixture was heated to 50° C. and treated with 3-Nitrobenzoyl chloride (63.2 g, 0.34 mol). The reaction that ensued was exothermic and caused the internal reaction temperature to rise to 65° C. The reaction was stirred for 50 min then bromobenzene (33.5 ml, 0.32 mol) was added. The reaction was heated at 90° C. for 3 h. Thin layer chromatographic analysis (Hexanes/ethylacetate 1:1) indicated completion of reaction. The reaction was cooled and ice-H2O (3 L) was added dropwise over a period of 1.5 h. The reaction was allowed to stir overnight. The solids were filtered, washed with H2O (1 L), saturated NaHCO3(aq) (1 L), another portion of H2O (500 mL) and Hexanes (500 mL). The product was dried in the vacuum oven at 40° C., 28 inHg for 30 hours to yield (4-Bromo-phenyl)-(3-nitro-phenyl)-methanone in 88% (85.34 g, 0.28 mol).

Workup

  1. customA 5 L, 3-necked round bottomed flask equipped with an overhead stirrer
  2. additionthe temperature was kept under 32° C. during the addition
  3. temperatureThe reaction mixture was heated to 50° C.
  4. customThe reaction
  5. customto rise to 65° C
  6. temperatureThe reaction was heated at 90° C. for 3 h
  7. customcompletion of reaction
  8. temperatureThe reaction was cooled
  9. stirringto stir overnight
  10. filtrationThe solids were filtered
  11. washwashed with H2O (1 L), saturated NaHCO3(aq) (1 L)
  12. customThe product was dried in the vacuum oven at 40° C.

Sources & evidence

ORD record
ord-c3112f86a47d4dc780d3861ba72c3134
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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