Hydrochloric Acid → 2-(2-Bromoethoxy)tetrahydro-2H-pyran

HRID 566529Notes

Reaction equation

HRID 566529 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][OH:10].Cl>>[Br:7][CH2:8][CH2:9][O:10][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 108982-Bromoethanol

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranYield 70.3%

Procedure

3,4-Dihydro-2H-pyran (92.5 g, 1.1 mol) was added dropwise to 2-bromoethanol (125 g, 1.0 mol) on an ice-bath. The temperature was kept between 25-30° C. during addition. When addition was complete a concentrated hydrochloric acid solution (1 ml) was added and the reaction mixture was stirred overnight at room temperature. The mixture was fractionated in vacuo to give 147 g (70%) of 2-bromoethyl- tetrahydropyran-2-yl ether.

Workup

  1. additionThe temperature was kept between 25-30° C. during addition
  2. additionWhen addition
  3. additionwas added

Sources & evidence

ORD record
ord-dbf128000c594d5fa35937200e5d6664
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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