Triethylamine → 2-Bromo-2,2-difluoroethyl 1-adamantanecarboxylate

HRID 909968Notes

Reaction equation

HRID 909968 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Br:14][C:15]([F:19])([F:18])[CH2:16][OH:17].C(N(CC)CC)C>O1CCCC1>[C:1]12([C:11]([O:17][CH2:16][C:15]([Br:14])([F:19])[F:18])=[O:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 183684762-Bromo-2,2-difluoroethan-1-ol

Product 1

HCID 591851612-Bromo-2,2-difluoroethyl 1-adamantanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran, 1-adamantanecarbonyl chloride and 2-bromo-2,2-difluoroethanol were mixed and ice cooled. Triethylamine was added to the mixture. By standard separation operation and solvent distillation, 2-bromo-2,2-difluoroethyl 1-adamantanecarboxylate was obtained. This compound was converted into a sodium sulfinate with sodium dithionite and then oxidized with hydrogen peroxide, yielding the target compound, sodium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethane-sulfonate.

Workup

  1. temperatureice cooled
  2. distillationBy standard separation operation and solvent distillation

Sources & evidence

ORD record
ord-b56ee627e91c43378e63a6b02d19c044
Source dataset
uspto-grants-2011_09
Patent number
US08021822B2

Reaction notes

Loading…