Triphenylphosphine → HCID 18786101, compound

HRID 629740Notes

Reaction equation

HRID 629740 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:23]=1[F:31]>C(#N)C>[Br-:20].[F:31][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:22]=1[CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 747792-(Bromomethyl)-1-fluoro-3-nitrobenzene

Product 1

HCID 18786101HCID 18786101, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine (31.2 g, 119 mmol) was added to a solution of 2-(bromomethyl)-1-fluoro-3-nitrobenzene (27.9 g, 119 mmol) in Acetonitrile (445 mL) (degassed with nitrogen) and the reaction stirred at ambient temperature for 10 min then heated to 85° C. for 2 hrs. The solvent was evaporated under reduced pressure to afford the title compound (59.1 g, 119 mmol, 100% yield) as a yellow powder, MS (ESI): m/z=416.2 (MH+); 100% pure by LCMS.

Workup

  1. temperaturethen heated to 85° C. for 2 hrs
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9aea03dbff354e95958a22ab5d11937c
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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