1,2-Dimethoxyethane → HCID 86611810, compound

HRID 1808307Notes

Reaction equation

HRID 1808307 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].B1(C=C)OB([CH:17]=[CH2:18])OB(C=C)O1.C1C=CN=CC=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>CCOC(C)=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.O>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([CH:17]=[CH2:18])[C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 678472-Chloro-6-fluorobenzaldehydeHCID 27348062,4,6-Trivinylboroxin-Pyridine Complex

Product 1

HCID 86611810HCID 86611810, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a vial charged with 2-chloro-6-fluorobenzaldehyde (158 mg, 1.0 mmol), 2,4,6-trivinylcyclotriboroxane pyridine complex (380 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (52 mg, 5 mol %) and potassium carbonate (280 mg, 2.0 mmol) was added a 3:1 mixture of 1,2-dimethoxyethane and water (2 mL). Upon completion of addition, the reaction was heated at 180° C. for 1 h under microwave conditions and then diluted with EtOAc (5 mL). The resulting mixture was washed with satd NaHCO3 (5 mL), dried over Na2SO4 and filtered. The volatiles were removed under reduced pressure to provide crude 2-fluoro-6-vinylbenzaldehyde. The crude 2-fluoro-6-vinylbenzaldehyde was dissolved in methanol (5 mL) and 10% palladium on carbon was added. The resulting reaction mixture was stirred under an atmosphere of H2 for 3 h and then filtered through celite. Once again, the volatiles were removed under reduced pressure to provide Intermediate 27 (approximately 300 mg) as a pale yellow oil, which was used without further purification.

Workup

  1. additionwas added
  2. additionUpon completion of addition
  3. washThe resulting mixture was washed with satd NaHCO3 (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-091eae9ba5d8488981ae84c72b187f09
Source dataset
uspto-grants-2013_01
Patent number
US08357809B2

Reaction notes

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