Trifluoromethanesulfonic acid → 2-Fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflate

HRID 1770180Notes

Reaction equation

HRID 1770180 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[OH:24].[F:25][C:26]([F:32])([F:31])[S:27](O)(=[O:29])=[O:28]>N1C=CC=CC=1>[O:24]([C:3]1[CH:4]=[CH:5][C:6]([C:8]2[N:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:13]=2)=[CH:7][C:2]=1[F:1])[S:27]([C:26]([F:32])([F:31])[F:25])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 1358112062-Fluoro-4-(5-decylpyrimidine-2-yl)phenol

Product 1

HCID 200950522-Fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflateYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.00 g (3.03 mM) of 2-fluoro-4-(5-decylpyrimidine-2-yl)phenol, 3 ml of pyridine were mixed and stirred on a common salt-ice bath. To the mixture, 1.00 ml (5.94 mM) of anhydrous trifluoromethanesulfonic acid was added dropwise and stirred for 20 minutes, followed by further stirring for 70 minutes at room temperature. After the reaction, the reaction mixture was left standing overnight and then was poured into ice water, followed by extraction with isopropyl ether. The isopropyl ether layer was successively washed with a common salt aqueous solution, 12%-HCl and a common salt aqueous solution, followed by drying with anhydrous sodium sulfate. The sodium sulfate was removed by filtration and the filtrate was concentrated into a solid product, whereby 1.32 g of 2-fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflate (Yield: 94.3%).

Workup

  1. stirringstirred for 20 minutes
  2. stirringby further stirring for 70 minutes at room temperature
  3. customAfter the reaction
  4. waitthe reaction mixture was left
  5. extractionfollowed by extraction with isopropyl ether
  6. washThe isopropyl ether layer was successively washed with a common salt aqueous solution, 12%-HCl
  7. dry with materialby drying with anhydrous sodium sulfate
  8. customThe sodium sulfate was removed by filtration

Sources & evidence

ORD record
ord-58534bdebaaa4e00922f2321a39dc071
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

Loading…