Triphenylphosphine → HCID 68690984, compound

HRID 1160381Notes

Reaction equation

HRID 1160381 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:31]([OH:35])[CH2:32][C:33]#[CH:34]>Cl[Pd]Cl.[Cu]I.C(NCC)C>[OH:35][CH2:31][CH2:32][C:33]#[C:34][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 11894Methyl 2-bromobenzoateHCID 135663-Butyn-1-OL

Product 1

HCID 68690984HCID 68690984, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

50 ml (0.36 M) of methyl 2-bromobenzoate, 930 mg (3.56 mM) of triphenylphosphine and 316 mg (1.78 mM) of PdCl2 are added to 1200 ml of diethylamine in a 2000 ml reactor. After stirring at room temperature for 5 minutes, 27 ml (0.36 M) of 3-butyn-1-ol and 680 mg (3.56 mM) of CuI (1) are added. The reaction medium is then stirred at 20° C. for 120 hours, the solvent is then evaporated off and the residue obtained is then purified by chromatography on silica, using dichloromethane as eluent. After evaporation, 46.7 g of a brown oil are thus obtained (64% yield).

Workup

  1. stirringThe reaction medium is then stirred at 20° C. for 120 hours
  2. customthe solvent is then evaporated off
  3. customthe residue obtained
  4. customis then purified by chromatography on silica
  5. customAfter evaporation, 46.7 g of a brown oil
  6. customare thus obtained (64% yield)

Sources & evidence

ORD record
ord-b9a0c1efc29b490d9781b4248768123f
Source dataset
uspto-grants-2010_10
Patent number
US07816397B2

Reaction notes

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