Chlorosuccinimide → 2-(2-Methoxy-5-bromophenyl)-2-methyl-1-chloropropyl methyl sulphide

HRID 444077

Reaction equation

HRID 444077 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][S:10][CH2:11][C:12]([C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:14])[CH3:13]>C(Cl)(Cl)(Cl)Cl>[CH3:9][S:10][CH:11]([Cl:1])[C:12]([C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 205362252-(2-Methoxy-5-bromophenyl)-2-methyl-1-propyl methyl sulphide

Product 1

HCID 205362412-(2-Methoxy-5-bromophenyl)-2-methyl-1-chloropropyl methyl sulphideYield 99%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

N-Chlorosuccinimide (37.4 g, 0.28 mole) was added portionwise to 2-(2-methoxy-5-bromophenyl)-2-methyl-1-propyl methyl sulphide (79.3 g, 0.275 mole) in carbon tetrachloride (250 ml) at room temperature. An exothermic reaction ensued, the temperature being allowed to rise to 40° C. before control with an external cooling bath was applied. After addition, the reaction mixture was heated at about 40° C. for 4 hours, then cooled, filtered and run down yielding 88 g crude title product (99%).

Workup

  1. customAn exothermic reaction
  2. customto rise to 40° C. before control with an external cooling bath
  3. additionAfter addition
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-45337b4c9852467493ce747f1f2ef810
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Linked notes

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