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

HRID 2197981Notes

Reaction equation

HRID 2197981 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-16b098776ac14c0581a0d8432ebf93b5
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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