Carbon Tetrachloride → 303779-69-3

HRID 1635948Notes

Reaction equation

HRID 1635948 reaction equation
C(Cl)(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:8]=[C:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCCCCC.C(OC(=O)C)C>[Br:25][CH2:17][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([Cl:6])[CH:8]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 186736453-Chloro-1-methylnaphthalene

Product 1

HCID 18673594303779-69-3Yield 84%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Carbon tetrachloride(30 ml) was added to 3-Chloro-1-methyl-naphthalene(2.55 g, 14.4 mmol) prepared in Preparation 36-1) and NBS (2.82 g, 15.8 mmol). A small quantity of benzoylperoxide was added as an initiator and the resulting mixture was heated under reflux for 3 hours. The reaction solution was cooled and filtered to remove the insoluble solid. The filtrate was concentrated and subjected to column chromatography(eluent: hexane/ethylacetate=95/5, v/v) to give 3.10 g(12.1 mmol, Yield 84%) of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction solution was cooled
  4. filtrationfiltered
  5. customto remove the insoluble solid
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1880a6fc705947da80dc564aa5cfd618
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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