Triphenylphosphine → HCID 15052465, compound

HRID 327610Notes

Reaction equation

HRID 327610 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17]O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17][Br:38])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 15052458HCID 15052458, compound

Product 1

HCID 15052465HCID 15052465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3.3 g (13.2 mmol) of 3-(3-cyclopentoxy-4-methoxyphenyl)-1-propanol in 75 mL of dry methylene chloride at 0° C. under a nitrogen atmosphere was added 4.3 g (16.4 mmol) of triphenylphosphine followed by a slow, portionwise addition of N-bromosuccinimide over a 5 minute period. The reaction mixture was stirred at 0° C. for 1.5 hours at the end of which time the mixture was quenched with excess methanol and stirred for an additional 10 minutes. Concentration of the mixture to dryness followed by liquid chromatography purification using 200 g of silica gel and elution 50% chloroform in hexane provided an analytically pure oil upon drying in vacuo.

Workup

  1. customwas quenched with excess methanol
  2. stirringstirred for an additional 10 minutes
  3. customConcentration of the mixture to dryness followed by liquid chromatography purification
  4. wash200 g of silica gel and elution 50% chloroform in hexane
  5. customprovided an analytically pure oil
  6. customupon drying in vacuo

Sources & evidence

ORD record
ord-0fb8574698544535930dd9f0db582871
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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