Triethylamine → 1-Adamantanecarboxylic acid

HRID 1801434Notes

Reaction equation

HRID 1801434 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.BrC(F)(F)C[OH:17].C(N(CC)CC)C>O1CCCC1>[C:1]12([C:11]([OH:12])=[O:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

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

Product 1

HCID 132351-Adamantanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-adamantanecarbonyl chloride and 2-bromo-2,2-difluoroethanol were mixed in tetrahydrofuran, and ice-cooled. Triethylamine was added into the mixture, and then a typical liquid separating operation and a distillation removal of solvent were conducted, to obtain 1-adamantanecarboxylic acid=2-bromo-2,2-difluoroethyl. Next, conversion into sodium sulfinate by sodium dithionite and oxidation by hydrogen peroxide were conducted for the mixture, to obtain intended sodium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate.

Workup

  1. temperatureice-cooled
  2. customa typical liquid separating operation
  3. distillationa distillation removal of solvent

Sources & evidence

ORD record
ord-6b714caa59b044fe90954e00b20c51b0
Source dataset
uspto-grants-2013_01
Patent number
US08349533B2

Reaction notes

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