Vinyl Acetate → HCID 67445064, compound

HRID 2092186Notes

Reaction equation

HRID 2092186 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Br:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][C:18]=1[OH:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:20](OC=C)(=O)[CH3:21]>C1(C)C=CC=CC=1>[Br:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][C:18]=1[O:19][CH:20]=[CH2:21])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 4778964Ethyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 67445064HCID 67445064, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a toluene (8 mL) solution of [IrCl(cod)]2 (54 mg, 0.08 mmol) and sodium carbonate (506 mg, 4.8 mmol) was added ethyl 3-bromo-4-hydroxybenzoate (CAS 37470-58-9) (1.95 g, 7.96 mmol) followed by vinyl acetate (1.5 mL, 15.9 mmol) under argon. The mixture was stirred at 100° C. for 2 hours. The mixture was cooled to room temperature, quenched with wet ether. Solid was filtered off and washed with ether. Column chromatography (3% ethyl acetate/hexane) gave ethyl 3-bromo-4-(vinyloxy)benzoate (1.77 g, 79%) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with wet ether
  3. filtrationSolid was filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-7c9d58159c8e46d0aa214f1b753772dc
Source dataset
uspto-grants-2013_05
Patent number
US08440698B2

Reaction notes

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