Triphenylphosphine → HCID 12217727, compound

HRID 1624439Notes

Reaction equation

HRID 1624439 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:22]1([C@H:28](O)[CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[Br:1][C@H:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:29]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 6375161-Phenylethanol, (R)-

Product 1

HCID 12217727HCID 12217727, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromine (3.2 g, 20.0 mmol) was added to a suspension of triphenylphosphine (5.2 g, 19.8 mmol) stirring in ACN at −15° C. The reaction was warmed to room temperature and stirred for 50 minutes then cooled to −35° C. and (R)-(+)-1-phenylethanol (1.6 g, 13.1 mmol) was added. The reaction was allowed to warm to −10° C. over 70 minutes and was then quenched with H2O and submitted to standard aqueous workup to afford the title compound which was used without further purification.

Workup

  1. temperaturethen cooled to −35° C.
  2. temperatureto warm to −10° C. over 70 minutes
  3. customwas then quenched with H2O

Sources & evidence

ORD record
ord-b43c5e9e0a4f435ca9e16b34276d1cee
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

Loading…