tert-Butyl hydroperoxide → 3-Chloromethylsulfonyl-2,5-dihydrofuran

HRID 2397646Notes

Reaction equation

HRID 2397646 reaction equation
ClCS(Br)(=O)=O.O1CC=CC1.C(OO)(C)(C)C.[Cl:18][CH2:19][S:20]([CH:23]1[CH:27](Br)[CH2:26][O:25][CH2:24]1)(=[O:22])=[O:21]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:18][CH2:19][S:20]([C:23]1[CH2:24][O:25][CH2:26][CH:27]=1)(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 155702,5-DihydrofuranHCID 12543458Chloromethanesulfonyl bromideHCID 125434603-Chloromethylsulfonyl-4-bromotetrahydrofuran

Product 1

HCID 125434643-Chloromethylsulfonyl-2,5-dihydrofuran

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

19.3 g (0.1 mole) of chloromethanesulfonic acid bromide are added in the course of 10 minutes to a solution of 14 g (0.2 mole) of 2,5-dihydrofuran and 0.5 ml of tert.-butyl hydroperoxide in 30 ml of chloroform at -40° C. After 15 minutes, 16.5 ml of triethylamine, dissolved in 20 ml of chloroform, are added dropwise at the same temperature, so as to dehydrobrominate the 3-chloromethylsulfonyl-4-bromotetrahydrofuran which has been formed. The mixture is stirred for half an hour at 20° C., washed with water, dried and concentrated. The residue is repeatedly digested with ether and the ether extract is distilled; it boils at 115°-120° C./0.2 mm Hg. 4.8 g of 3-chloromethylsulfonyl-2,5-dihydrofuran are obtained.

Workup

  1. additionare added dropwise at the same temperature
  2. customhas been formed
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. extractionthe ether extract
  7. distillationis distilled

Sources & evidence

ORD record
ord-c69709345a124c82a16b49248c049f35
Source dataset
uspto-grants-1977_05
Patent number
US04022804

Reaction notes

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