Bromochloromethane → HCID 86175238, compound

HRID 326779Notes

Reaction equation

HRID 326779 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][O:3][CH2:4][C:5]([O-:7])=[O:6].BrCCl.[CH2:15]([Cl:17])[Cl:16]>>[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][O:3][CH2:4][C:5]([O:7][CH:15]([Cl:17])[Cl:16])=[O:6]

Participants

4

Reactant 3

HCID 6333BromochloromethaneHCID 6344DichloromethaneHCID 86747410HCID 86747410, compound

Product 1

HCID 86175238HCID 86175238, compoundYield 10%

Procedure

A solution of the tetrabutylammonium salt of monoethyl diglycolate (16 g, 0.04 mol) in methylene chloride (125 ml) was added to bromochloromethane (200 ml) over 1.5 hr. The resulting solution was stirred at room temperature overnight and then evaporated to dryness. The residue was chromatographed on silica eluting with ethyl acetate/hexane, 40/60 and the fractions containing product combined and evaporated to give ethyl dichloromethyl diglycolate (0.836 g, 10%) as a colorless oil. NMR analysis showed the material to be approximately 70% pure, but was used directly in the next step.

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed on silica eluting with ethyl acetate/hexane, 40/60
  3. additionthe fractions containing product
  4. customevaporated

Sources & evidence

ORD record
ord-fb1326db34a246cab163b1b227b9e1c2
Source dataset
uspto-grants-1993_12
Patent number
US05270331

Reaction notes

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