(4-(Decyloxy)phenyl)boronic acid → (R)-(-)-3-Cyano-4'-Decyloxy-4-(1-methylheptyloxy)biphenyl

HRID 1066556Notes

Reaction equation

HRID 1066556 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:19]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>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.C(=O)([O-])[O-].[Na+].[Na+]>[C:7]([C:6]1[CH:9]=[C:2]([C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=2)[CH:3]=[CH:4][C:5]=1[O:10][C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])#[N:8]

Participants

5

Reactant 2

HCID 10612601(4-(Decyloxy)phenyl)boronic acidHCID 53905579(R)-(-)-5-Bromo-2-(1-methylheptyloxy)benzonitrile

Product 1

HCID 54294552(R)-(-)-3-Cyano-4'-Decyloxy-4-(1-methylheptyloxy)biphenyl

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

Quantities: compound 42 (1.50 g, 4.84 mmol), compound 87 (1.61 g, 5.81 mmol), aqueous sodium carbonate (2 M, 20 ml), tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.24 mmol),

Sources & evidence

ORD record
ord-ae64c6f32b73459fbc0dad884163f9a4
Source dataset
uspto-grants-2001_06
Patent number
US06242636B1

Reaction notes

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