Sulfuric Acid → 3-Chlorobenzophenone

HRID 851300

Reaction equation

HRID 851300 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([Cl:9])[CH:6]=[CH:7][CH:8]=1.[C:10](#N)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)[OH:19]>O1CCCC1>[Cl:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 79281-Bromo-3-chlorobenzeneHCID 5462224Magnesium

Product 1

HCID 660983-Chlorobenzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 6.4 g. (0.266 mole) of magnesium turnings in 50 ml. of tetrahydrofuran was added dropwise 51 g. (0.268 mole) of 3-bromochlorobenzene in 100 ml. of dried tetrahydrofuran and the mixture refluxed for one hour. The cooled reaction mixture was added to 27.4 g. (0.266 mole) of benzonitrile in 100 ml. of tetrahydrofuran and refluxed for one hour. The reaction mixture was poured carefully into 100 ml. of ice/water and 10 ml. of concentrated sulfuric acid and heated on a steam bath for 30 minutes. The solution was cooled, extracted with ether, washed with water and 5% sodium bicarbonate solution, dried, evaporated and chromatographed to give 3-chlorobenzophenone (recrystallized from methanol), m.p. 83° C.

Workup

  1. additionTo a suspension of 6.4 g
  2. customThe cooled reaction mixture
  3. additionwas added to 27.4 g
  4. additionThe reaction mixture was poured carefully into 100 ml
  5. temperatureThe solution was cooled
  6. extractionextracted with ether
  7. washwashed with water and 5% sodium bicarbonate solution
  8. customdried
  9. customevaporated
  10. customchromatographed

Sources & evidence

ORD record
ord-1f2fe66ee6674471b44355f9fff00fa4
Source dataset
uspto-grants-1983_05
Patent number
US04383999

Linked notes

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