Triphenylphosphine → (1-Cyanocyclopropyl)-2-bromomethylcyclohexanecarboxamide

HRID 2222940Notes

Reaction equation

HRID 2222940 reaction equation
[C:1]([C:3]1([C:6]2([C:14]([NH2:16])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]2[CH2:12]O)[CH2:5][CH2:4]1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>O1CCCC1>[C:1]([C:3]1([C:6]2([C:14]([NH2:16])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]2[CH2:12][Br:36])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 69114725(1-Cyanocyclopropyl)-2-hydroxymethyl-cyclohexane-carboxamide

Product 1

HCID 69115024(1-Cyanocyclopropyl)-2-bromomethylcyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1-Cyanocyclopropyl)-2-hydroxymethyl-cyclohexane-carboxamide was dissolved, along with triphenylphosphine (2.77 g, 10.58 mmol) in tetrahydrofuran (100 mL) (Note—heating was required to effect dissolution). The reaction mixture was cooled carefully in an ice/water bath, ensuring the solution remained homogeneous. N-bromosuccinimide (1.88 g, 10.58 mmol) was added in small portions. Once a clear solution had formed, the cooling bath was removed, and the reaction mixture was permitted to stir overnight. The solvent was evaporated and the residue was purified on a short plug of silica gel (30-60% ethyl acetate/hexane) to give (1-cyanocyclopropyl)-2-bromomethylcyclohexanecarboxamide. MS [ESI, (M+H)+] m/z=285, 287.

Workup

  1. temperatureThe reaction mixture was cooled carefully in an ice/water bath
  2. customOnce a clear solution had formed
  3. customthe cooling bath was removed
  4. customThe solvent was evaporated
  5. customthe residue was purified on a short plug of silica gel (30-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b36f6165c0d443693effbda46229e35
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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