Trifluoroacetic acid → HCID 17993205, compound

HRID 1491505Notes

Reaction equation

HRID 1491505 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 in 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 crystallization 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 crystallization in isooctane

Sources & evidence

ORD record
ord-6bdc29b3e45e4697bc813769e58ea8b9
Source dataset
uspto-grants-1994_12
Patent number
USRE034805

Reaction notes

Loading…