Triphenylphosphine → HCID 57771478, compound

HRID 2070556Notes

Reaction equation

HRID 2070556 reaction equation
[CH:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][C:2]=1[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:32][CH2:11][C:2]1[CH2:3][CH2:4][C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:1]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57771564HCID 57771564, compound

Product 1

HCID 57771478HCID 57771478, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of spiro[4.5]dec-1-en-2-yl-methanol (50 mg) obtained in Step 5 in chloroform (1 mL) were added triphenylphosphine (87 mg) and N-bromo-succinimide (87 mg) under ice-cooling, followed by stirring the reaction mixture at room temperature for 1 hour. Then, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane) to give 2-bromomethyl-spiro[4.5]dec-1-ene (55 mg).

Workup

  1. temperaturecooling
  2. concentrationThen, the reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-96beb8d2cfb94cff91a6c6d4a23a872c
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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