Ethanol → Methyl 3-phenylbenzoate

HRID 2421613Notes

Reaction equation

HRID 2421613 reaction equation
Br[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(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:12]1([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 702EthanolHCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 66827Phenylboronic Acid

Product 1

HCID 9855857Methyl 3-phenylbenzoateYield 9,853.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Using Preparation Method 2, Methyl 3-bromobenzoate (3.86 g, 18.6 mmol) was reacted with phenyl boronic acid (2.4 g, 20.5 mmol) in the presence of 5 mol % Pd(PPh3)4, 18 mL of 2N Na2CO3, 9.4 mL of Ethanol and 37 mL of toluene. The resulting reaction mixture was purified using SiO2 with hexane/diethyl ether 98:2 to give a colourless thick oil (389 g, 96%). NMR 1H (ppm, CDCl3): 8.29 (s, 1H), 8.03 (d, J3=7.8 Hz, 1H), 7.79 (d, J3=7.8 Hz, 1H), 7.63 (d, J3=7.2 Hz, 2H), 7.54-7.26 (m, 4H), 3.96 (s, 3H). MS: M+1 463.2.

Workup

  1. customThe resulting reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-44465c0cd0ea4f7e97eb01b4606f871d
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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