Phenylboronic Acid → N-n-propyl-4-phenylbenzamide

HRID 2421599Notes

Reaction equation

HRID 2421599 reaction equation
[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH2:2][CH3:3].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 31133444-bromo-N-propylbenzamide

Product 1

HCID 4172958N-n-propyl-4-phenylbenzamideYield 71%

Procedure

Using Preparation Method 2, N-n-propyl-4-bromobenzamide from Example 9A was reacted with phenylboronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2/Petroleum Ether 80:20 to CH2Cl2/AcOH 80:20 to give a white solid (71%). NMR 1H (ppm, CDCl3): 7.82 (d, J3=8.32 Hz, 2H), 7.63 (d, J3=8.69 Hz, 2H), 7.59 (d, J3=7.14 Hz, 2H), 7.45 (t, J3=7.09 Hz, 2H), 7.39-7.34 (m, 1H), 6.14 (br. s., 1H), 3.47-3.41 (m, 2H), 1.65 (sext., J3=7.18 Hz, 2H), 0.99 (t, J3=7.37 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-cff80522bbe7425ea71067039a359ce1
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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