Triphenylphosphine → HCID 12217727, compound

HRID 1183392Notes

Reaction equation

HRID 1183392 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-548a813ceaad4b39a36a9e6cddbe3cfd
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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