Water → HCID 22172362, compound

HRID 1823196Notes

Reaction equation

HRID 1823196 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].O.B1(C=C)OB([CH:29]=[CH2:30])OB(C=C)O1.C1C=CN=CC=1>C(COC)OC.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>[CH:29]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=2)[CH:3]=1)=[CH2:30]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 27348062,4,6-Trivinylboroxin-Pyridine Complex

Product 1

HCID 22172362HCID 22172362, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 6-bromo-2-naphthalene carboxylate (98 g) was dissolved in dimethoxyethane (2 1) and tetrakis(triphenylphosphine)palladium (44 g) was added in nitrogen atmosphere. The mixture was stirred for 30 minutes at room temperature. Potassium carbonate (52 g), water (1 1) and 2,4,6-trivinylcyclotriboroxane-pyridine complex (91 g) were added and the mixture was stirred for 24 hours while refluxing with heating. There action mixture was cooled to room temperature and treated with activated alumina to obtain methyl 2-vinyl-6-naphthalene carboxylate (77 g).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. temperaturewhile refluxing
  3. temperaturewith heating
  4. temperatureThere action mixture was cooled to room temperature
  5. additiontreated with activated alumina

Sources & evidence

ORD record
ord-3c64090ec318462abb36a7d794fa46a3
Source dataset
uspto-grants-2006_05
Patent number
US07037994B2

Reaction notes

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