Water → 2-(3-Isopropenyl-phenyl)-[1,3]dioxolane

HRID 1946925Notes

Reaction equation

HRID 1946925 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[C:13](B1OC(C)(C)C(C)(C)O1)([CH3:15])=[CH2:14].C(=O)([O-])[O-].[Na+].[Na+].O>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>[C:13]([C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1)([CH3:15])=[CH2:14]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 666497742-(3-Isopropenyl-phenyl)-[1,3]dioxolaneYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A degassed solution of 2-(3-bromo-phenyl)-[1,3]dioxolane (3.46 ml, 22.6 mmol) in dimethoxyethane (60 ml) was added into a tube which has been charged with a mixture of 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.8 g, 22.6 mmol) and an aqueous solution of sodium carbonate (1M, 20 ml); tetrakis(triphenylphosphine)palladium(0) (0.266 g) is then added, the tube is sealed and heated to 90° C. overnight. After cooling of the reaction mixture, water (20 ml) was added, the aqueous layer separated and extracted with dichloromethane (3×20 ml). The combined organic layers were dried over sodium sulphate and evaporated. The crude product was purified by chromatography on silica gel using cyclohexane as the eluent. There were obtained 2.85 g (68% of theory) of the 2-(3-isopropenyl-phenyl)-[1,3]dioxolane.

Workup

  1. customthe tube is sealed
  2. additionwas added
  3. customthe aqueous layer separated
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. customevaporated
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ff5f72dac3ad421e87041024a73476d1
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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