Chloromethyl Methyl Ether → 4-Chloromethylbenzocyclobutene

HRID 2372574Notes

Reaction equation

HRID 2372574 reaction equation
[CH2:1]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=[C:3]2[CH2:2]1.CO[CH2:11][Cl:12].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:12][CH2:11][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[CH2:1][CH2:2][C:3]=12

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24287Tin tetrachlorideHCID 69667Benzocyclobutene

Product 1

HCID 126177184-ChloromethylbenzocyclobuteneYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10 g of benzocyclobutene and 18.25 mL of chloromethyl methyl ether in 100 mL of methylene chloride at -78° C. under a nitrogen atmosphere, 11.1 g tin tetrachloride was added slowly over a period 1 hour and stirring was continued for 6 more hours at -78° C. The reaction mixture was then poured into an ice cold sodium hydroxide solution (10%) and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Removal of the solvent followed by purification by flash chromatography afforded 6 g of 4-chloromethylbenzocyclobutene (41%) as a colorless liquid.

Workup

  1. customwas continued for 6 more hours at -78° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent
  6. customfollowed by purification by flash chromatography

Sources & evidence

ORD record
ord-7c279bf5cf0049afbb7f08dfd7fb273c
Source dataset
uspto-grants-1992_03
Patent number
US05099083

Reaction notes

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