Sodium hydride → 2-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile
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+].F[C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[C:16]=1[C:17]#[N:18]>CN(C)C(=O)C.CCOCC>[Br:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:15]([S:11][C:1]23[CH2:8][CH:7]4[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]4)[CH2:2]2)[CH2:10]3)[C:16]=1[C:17]#[N:18]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of adamantanethiol (1.01 g) in N,N-dimethylacetamide (20 mL) at room temperature was added NaH (0.24 g, 60% in mineral oil) and the reaction was stirred for 10 minutes. 2-Fluoro-6-bromobenzonitrile (1 g) was added and the mixture was heated to 80° C. for 1 hour. The reaction mixture was cooled and diluted with ether (400 mL), and the mixture was washed three times with 1M NaOH solution and once with brine, then dried over sodium sulfate, filtered and concentrated to yield the crude product which was taken on to the next step without purification.
Workup
- temperatureThe reaction mixture was cooled
- washthe mixture was washed three times with 1M NaOH solution
- dry with materialonce with brine, then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6530d3761b4c42d7bd2b4e3ef6d62aa1
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227963B2
Reaction notes
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