Diethyl Ether → 2-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile

HRID 588674Notes

Reaction equation

HRID 588674 reaction equation
[C:1]12([SH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18].C(OCC)C>CS(C)=O>[C:1]12([S:11][C:19]3[CH:20]=[CH:21][CH:22]=[C:15]([Br:14])[C:16]=3[C:17]#[N:18])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 997301-AdamantylthiolHCID 27831392-Bromo-6-fluorobenzonitrile

Product 1

HCID 866812652-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Adamantanethiol (278 mg) was dissolved in dimethyl sulfoxide (10 mL). Sodium hydride (60% in mineral oil, 42 mg) was added, and the solution was stirred at room temperature for 20 minutes. 2-Bromo-6-fluorobenzonitrile (300 mg) was added and the solution was heated to 130° C. for 1 hour. The solution was cooled, added to diethyl ether, washed with 1 M aqueous HCl three times, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed under vacuum to yield the title compound.

Workup

  1. temperaturethe solution was heated to 130° C. for 1 hour
  2. temperatureThe solution was cooled
  3. washwashed with 1 M aqueous HCl three times
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-dcebbb6d583647d1a08d12839ff7babc
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

Loading…