Dichloromethane → METHYL 3-PHENYLETHYNYL-BENZOATE

HRID 2421650Notes

Reaction equation

HRID 2421650 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1([C:18]#[CH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCCC1.C(Cl)Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:12]1([C:18]#[C:19][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 10821PhenylacetyleneHCID 69258Methyl 3-iodobenzoate

Product 1

HCID 11053642METHYL 3-PHENYLETHYNYL-BENZOATE

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

Methyl 3-iodobenzoate, phenylacetylene (1.5 eq.) and Pd(PPh3)2Cl2 (5 mol %) in piperidine (3 eq.) was heated at 70° C. for 30 minutes. The solidified residue was dissolved with CH2Cl2 and water and poured onto HCl 2N. The acidic phase was extracted three times with CH2Cl2. The combined organic layers were washed twice with HCl 2N, once with water and once with brine. The organic layer was then dried over MgSO4 and concentrated. The resulting residue was purified using SiO2 with petroleum spirit/toluene 70:30 to give methyl 3-phenylethynyl-benzoate as a white solid (quantitative yield). NMR 1H (ppm, CDCl3): 8.20 (t, J4=1.7 Hz, 1H), 7.98 (d, J3=7.9 Hz, 1H), 7.69 (d, J3=7.6 Hz, 1H), 7.54-7.50 (m, 2H), 7.42 (t, J3=7.8 Hz, 1H), 7.36-7.31 (m, 3H), 3.92 (s, 3H).

Workup

  1. additionpoured onto HCl 2N
  2. extractionThe acidic phase was extracted three times with CH2Cl2
  3. washThe combined organic layers were washed twice with HCl 2N, once with water and once with brine
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-9c63c7a6521247f89e8537bf746ca42c
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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