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Triethylamine → 1-(4-Carbo-tert.-butoxyphenyl)-2-(4'-carbethoxy-biphenyl-4-yl)-ethyne

HRID 974218
Notes
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Reaction equation

HRID 974218 reaction equation
C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.[C:45]([O:49][C:50](=[O:59])[C:51]1[CH:56]=[CH:55][C:54]([C:57]#[CH:58])=[CH:53][CH:52]=1)([CH3:48])([CH3:47])[CH3:46]>C(#N)C.[Cu]I>[C:50]([C:51]1[CH:56]=[CH:55][C:54]([C:57]#[C:58][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)=[CH:53][CH:52]=1)([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:59]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 13965008Tert-butyl 4-ethynylbenzoateHCID 14924841Ethyl 4'-bromo-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 199856561-(4-Carbo-tert.-butoxyphenyl)-2-(4'-carbethoxy-biphenyl-4-yl)-ethyne

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6342AcetonitrileSolvent2×

Procedure

100 ml of triethylamine, 6.3 g of triphenylphosphine, 2.81 g of (Pφ3)2PdCl2 and 0.77 g of copper(I)iodide are added under nitrogen to 61 g of 4-bromo-4'-carbethoxybiphenyl in 300 ml of absolute acetonitrile. 44.3 g of 4-ethinyl-benzoic acid tert.-butyl ester dissolved in 300 ml of absolute acetonitrile are slowly added dropwise at the reflux temperature and the reaction mixture is boiled overnight. It is then suction filtered while hot and stirred up in water and again suction filtered and the residue is dissolved in CH2Cl2 and filtered after the addition of Tonsil.

Workup

  1. additionare slowly added dropwise at the reflux temperature
  2. filtrationsuction filtered while hot and
  3. filtrationagain suction filtered
  4. dissolutionthe residue is dissolved in CH2Cl2
  5. filtrationfiltered
  6. additionafter the addition of Tonsil

Sources & evidence

ORD record
ord-a5fd330612ed43fb9ecb981cf2f9d948
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05068300

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes