Dicyclohexylamine → HCID 68459222, compound

HRID 2358811Notes

Reaction equation

HRID 2358811 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C1(B(O)[OH:19])C=CC=CC=1.[CH:21]1([NH:27][CH:28]2[CH2:33]CCCC2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CCCCCCCCCCC>C1(C)C=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([NH:27][C:28](=[O:19])[CH3:33])[CH:22]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 7582DicyclohexylamineHCID 14257UndecaneHCID 66827Phenylboronic AcidHCID 792244-Bromo-3-nitrotoluene

Product 1

HCID 68459222HCID 68459222, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Bromo-4-methyl-2-nitro-benzene (0.107 g, 0.49 mmol) was reacted as described in Example 215a substituting 3-acetamidophenylboronic acid (0.086 g, 0.49 mmol) for phenylboronic acid, dicyclohexylamine (4 mole %) for 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3.]undecane and substituting dioxane for toluene to give the title biphenyl (0.0552 g, 42%).

Sources & evidence

ORD record
ord-4b58614b71ef422c8d461abf21cc8283
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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