Phenylboronic Acid → 5-Methyl-2-nitro-1,1'-biphenyl

HRID 2358816

Reaction equation

HRID 2358816 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 81670382-Bromo-4-methyl-1-nitrobenzene

Product 1

HCID 543942305-Methyl-2-nitro-1,1'-biphenylYield 94.3%

Procedure

The product from Example 219a (0.20 g, 0.93 mmol) was reacted with phenylboronic acid (0.135 g, 1.11 mmol) for 19.5 h at 80° C. as described in Example 218a. The reaction mixture was cooled and filtered through celite, the filtrate concentrated under vacuum to give the crude product which was purified by flash chromatography on silica gel to give the title biphenyl (0.187 g, 94%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationthe filtrate concentrated under vacuum
  4. customto give the crude product which
  5. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e22b4eb59695478e880da06fdf1885bc
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Linked notes

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