Bromomethylcyclopropane → HCID 68681688, compound

HRID 1865474Notes

Reaction equation

HRID 1865474 reaction equation
[CH:1]1([CH2:4][S:5][CH:6]2[CH2:11][CH2:10][CH:9]([C:12]#[N:13])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>C1COCC1>[CH:14]1([CH2:17][C:9]2([C:12]#[N:13])[CH2:10][CH2:11][CH:6]([S:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:7][CH2:8]2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68682374HCID 68682374, compound

Product 1

HCID 68681688HCID 68681688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile (either isomer) (1.95 g; 10 mmol) was dissolved in THF (10 mL) and cyclopropyl methyl bromide (2.7 g; 20 mmol) was added followed by the dropwise addition of sodium hexamethyldisilazide (2M, 10 mL, 20 mmol). The reaction was stirred for half an hour and then was quenched with brine and extracted into ethyl acetate. The organic layer was dried and product was purified rigorously from its less polar isomer on silica using a Biotage 65i cartridge eluting with EtOAc/isohexane to yield 1-(cyclopropylmethyl)4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile as an oil. (2 g, 80%)

Workup

  1. customwas quenched with brine
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was dried
  4. customproduct was purified rigorously from its less polar isomer on silica using a Biotage 65i cartridge
  5. washeluting with EtOAc/isohexane

Sources & evidence

ORD record
ord-ebd8361812214a70b654b6c46c0c559a
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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