Water → methyl 4-(phenylethynyl)benzoate

HRID 227928Notes

Reaction equation

HRID 227928 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:19]([O-])([O-])=O.[Cs+].[Cs+].O>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(S([O-])(=O)=O)=CC=2C(C)C)CCCCC1.[Na+].C(#N)C>[CH3:19][O:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([C:18]#[C:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63184-Chlorobenzoic AcidHCID 10796Cesium carbonateHCID 10821Phenylacetylene

Product 1

HCID 11172410methyl 4-(phenylethynyl)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 23674066Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropyl-[1,1'-biphenyl]-4-sulfonateCatalystHCID 6342AcetonitrileSolvent

Procedure

The general procedure described in Example 27 was used with 4-chlorobenzoic acid (79 mg, 0.50 mmol), phenylacetylene (0.072 mL, 0.65 mmol), PdCl2(CH3CN)2 (3.2 mg, 0.0125 mmol, 1.25 mol %), sodium 2′-(dicyclohexyl-phosphanyl)-2,6-diisopropyl-biphenyl-4-sulfonate (20.0 mg, 0.0375 mmol, 3.75 mol %), Cs2CO3 (650 mg, 2.00 mmol), water (1.0 mL), acetonitrile (1.5 mL), 12 h, 100° C. The product was isolated as a white solid (101 mg, 86%). Mp=114° C. (lit. 113-115° C.). 1H NMR (400 MHz, CDCl3) δ: 8.04 (d, 2H, J=8.4 Hz), 7.61 (d, 2H, J=8.4 Hz), 7.57 (m, 2H), 7.39 (m, 3H). 13C NMR (125 MHz, CDCl3) δ: 166.6, 131.9, 131.6, 129.64, 129.56, 128.9, 128.6, 128.1, 122.8, 92.5, 88.8, 52.3.

Sources & evidence

ORD record
ord-76f7950519a54da8899cfdd73de1d93e
Source dataset
uspto-grants-2009_07
Patent number
US07560596B2

Reaction notes

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