Bromine → HCID 13048612, compound

HRID 1701996Notes

Reaction equation

HRID 1701996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Br:25]Br>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:25][CH:9]([C:10](=[O:15])[C:11]([CH3:14])([CH3:12])[CH3:13])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 24408BromineHCID 13048611HCID 13048611, compound

Product 1

HCID 13048612HCID 13048612, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

1-(4-Chlorophenyl)-4,4-dimethyl-1-phenylsulfonylpentan-3-one (5.0 g) was dissolved in a mixture of 100 ml of chloroform and 100 ml of acetic acid. To this solution, 2.2 g of bromine was added dropwise at 50° C. The mixture was kept at 50° C. for 3 hours and then washed with ice-water and an aqueous solution of sodium bicarbonate. The chloroform layer was evaporated and the solid residue was crystallized in a mixture of carbon tetrachloride and n-hexane. The crystals were collected by filtration and dried to give 5.8 g of the captioned compound. m.p. 167°-168° C.

Workup

  1. washwashed with ice-water
  2. customThe chloroform layer was evaporated
  3. customthe solid residue was crystallized in a mixture of carbon tetrachloride and n-hexane
  4. filtrationThe crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-6ee7b848c65345148a74ef245c5b1838
Source dataset
uspto-grants-1983_04
Patent number
US04379921

Reaction notes

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