HCID 17829551, compound → HCID 68421412, compound

HRID 645309Notes

Reaction equation

HRID 645309 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12](Br)=[CH:13][CH:14]=2)[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:22][CH:23]([CH2:37][CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1>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.C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:30]3[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH:23]([CH3:22])[CH2:37][CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:28][CH:29]=3)=[CH:13][CH:14]=2)[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 17829551HCID 17829551, compoundHCID 67458210HCID 67458210, compound

Product 1

HCID 68421412HCID 68421412, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22272177Toluene waterSolvent

Procedure

Under argon atmosphere and in a toluene/water mixed solvent, 6-bromonaphthalene-1,4-dicarboxylic-acid diethyl ester 4.5 g and 4-(3,7-dimethyloctyloxy)phenyl boric acid 4.0 g were reacted with using tetrakis(triphenylphosphine)palladium under a condition of usual Suzuki reaction. Purification by column treatment (silica gel/toluene) was carried out, and 6-(4-(3,7-dimethyloctyloxy)phenyl)naphthalene-1,4-dicarboxylic-acid diethyl ester 3.5 g was obtained.

Workup

  1. customPurification by column treatment (silica gel/toluene)

Sources & evidence

ORD record
ord-b3c2873fdb8a4c02b586e8cc08ea603d
Source dataset
uspto-grants-2010_04
Patent number
US07701129B2

Reaction notes

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