Triphenylphosphine → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

HRID 1382424Notes

Reaction equation

HRID 1382424 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[CH:15])[CH:5]=[CH:4][C:3]1=2.Br[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 147265491,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 4 g (19 millimoles) of (5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethyne, 2.8 g (12.5 millimoles) of 4-bromobenzonitrile, 50 mg of palladium (II) acetate, 100 mg of triphenylphosphine and 25 ml of degased anhydrous triethylamine was refluxed for 4 hours under nitrogen. Thereafter, solid material was filtered off and the filtrate was evaporated down.

Workup

  1. temperaturewas refluxed for 4 hours under nitrogen
  2. filtrationThereafter, solid material was filtered off
  3. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-1e2458372ac048c4b73f23baeaf769cc
Source dataset
uspto-grants-1989_02
Patent number
US04806558

Reaction notes

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