Trifluoroacetic acid → HCID 17993205, compound

HRID 2081248Notes

Reaction equation

HRID 2081248 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[C:9]12(O)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O>[C:9]12([S:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 641521-AdamantanolHCID 660494-BromothiophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 17993205HCID 17993205, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.78 g (20 mmol) of p-bromothiophenol, 3.04 g (20 mmol) of 1-adamantanol and 10 ml of trifluoroacetic acid are stirred at ambient temperature for 8 hours and then poured into water. Sodium bicarbonate is added until the mixture is neutral at which time it is extracted with methylene chloride. The organic phase is dried and evaporated. After recrystallization in isooctane, 5.9 g of the expected product are obtained. Yield--92%. Melting point: 121°-122° C.

Workup

  1. extractionis extracted with methylene chloride
  2. customThe organic phase is dried
  3. customevaporated
  4. customAfter recrystallization in isooctane

Sources & evidence

ORD record
ord-30e906466d264570bfb31fc1c0c3f3d0
Source dataset
uspto-grants-1993_02
Patent number
US05183889

Reaction notes

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