Dichloromethane → Naphthalene, 1-chloro-2-methyl-

HRID 580913Notes

Reaction equation

HRID 580913 reaction equation
[Sn].C[Sn](C)(C)[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH3:14].C(Cl)[Cl:18]>>[Cl:18][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH3:14]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 5352426Tin atomHCID 13668051HCID 13668051, compound

Product 1

HCID 138615Naphthalene, 1-chloro-2-methyl-Yield 80%

Procedure

To the tin compound 20 (1 g, 3.3 mmole) in CH2Cl2 (50 ml) was added N-chlorosuccimimide NCIS (931 mg, 7 mmole). The mixture was stirred overnight. The mixture was washed with saturated solution of NaHCO3, water, brine, dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield 0.7 g of a crude yellowish semi-solid. The crude yellow semi-solid was purified by column chromatography (silica, 100% hexane) to afford 1.2 g of 21 (80%) as a white powder. A simple component was detected by TLC (100%) hexane) Rf, 0.69; NMR (CDCl3) d 2.3 (3H, S, CH3), d 7.2-8.2 (m, 6H, naphthyl).

Workup

  1. washThe mixture was washed with saturated solution of NaHCO3, water, brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto yield 0.7 g of a crude yellowish semi-solid
  5. customThe crude yellow semi-solid was purified by column chromatography (silica, 100% hexane)

Sources & evidence

ORD record
ord-059e8ab3e1024c508c15560449b374a7
Source dataset
uspto-grants-1999_07
Patent number
US05919797

Reaction notes

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