Nitrogen → Diethyl 2,5-dinaphth-1-ylterephthalate

HRID 1425615Notes

Reaction equation

HRID 1425615 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[C:16](Br)=[C:17]([CH:23]=[CH:24][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].N#N>C1(C)C=CC=CC=1.O.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.CCO>[C:1]1([C:24]2[CH:23]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([C:9]3[C:10]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[CH:6]=[CH:7][CH:8]=3)=[CH:15][C:25]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 66645638Diethyl dibromoterephthalate

Product 1

HCID 57782612Diethyl 2,5-dinaphth-1-ylterephthalate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

193.3 g (0.82 mol) of naphthylboronic acid, 180.4 g (474 mmol) of diethyl dibromoterephthalate and 315.9 g (2-29 mol) of potassium carbonate are initially introduced in a mixture of 850 ml of toluene and 850 ml of water and saturated with N2 for 30 min. After addition of 1.36 g (1.18 mmol) of Pd(PPh3)4, the mixture is heated at the boil for 4 h. After cooling to RT and addition of 400 ml of EtOH, the mixture is cooled to room temperature and stirred for 1 h, and the precipitate is filtered off with suction, washed with water, EtOH and heptane and dried at 80° C. in vacuo. The yield of colourless solid is 160.7 g (71%).

Workup

  1. temperaturethe mixture is heated at the boil for 4 h
  2. temperaturethe mixture is cooled to room temperature
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with water, EtOH and heptane
  5. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-b31f1387ddfb4ff4887bebc258b802c2
Source dataset
uspto-grants-2015_01
Patent number
US08932732B2

Reaction notes

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