Nitrogen → Dimethyl 2-(4-methylnaphthalen-1-yl)isophthalate

HRID 1397653Notes

Reaction equation

HRID 1397653 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:16]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.CCO.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.O.CO>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:16]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 126993601,3-Benzenedicarboxylic acid, 2-bromo-, 1,3-dimethyl ester

Product 1

HCID 58260548Dimethyl 2-(4-methylnaphthalen-1-yl)isophthalate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

35 g (148 mmol) of 4-methylnaphthaleneboronic acid, 33.8 g (124 mmol) of dimethyl 2-bromoisophthalate and 220 ml of 2 M Na2CO3 solution are suspended in 1 l of toluene and 1 l of EtOH, the mixture is saturated with N2, 2.9 g (3 mmol) of tetrakis(triphenylphosphine)palladium(0) are added, and the mixture is heated at the boil for 2 h. The mixture is poured into 3 l of a mixture of water/MeOH/6 M HCl 1:1:1, the beige precipitate is filtered off with suction, washed with water, EtOH and toluene and dried. The content of product according to 1H-NMR is about 95% with an overall yield of 37 g (90%).

Workup

  1. additionare added
  2. temperaturethe mixture is heated at the boil for 2 h
  3. filtrationthe beige precipitate is filtered off with suction
  4. washwashed with water, EtOH and toluene
  5. customdried

Sources & evidence

ORD record
ord-82f6abfd36cd4cf1b7e611979f23d7fc
Source dataset
uspto-grants-2014_12
Patent number
US08901298B2

Reaction notes

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