1,2-Dimethoxyethane → Tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate

HRID 2191618Notes

Reaction equation

HRID 2191618 reaction equation
CO[CH2:3][CH2:4]OC.Br[C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:9]=1.C(B1OC(C)(C)C(C)(C)O1)=C.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1>[F:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:10]2[CH:9]=[C:8]([CH:3]=[CH2:4])[CH:20]=[CH:19][C:11]=2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68959213Tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a mixed solution of ethylene glycol dimethyl ether 50 mL and water 15 mL of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 5.0 g were added vinylboronic acid pinacol ester 2.7 mL, potassium carbonate 2.3 g and tetrakis(triphenylphosphine)palladium(0) 0.80 g at room temperature sequentially, and it was heated and refluxed under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, toluene and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=20:1] to give tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 3.4 g of yellow oil.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 4 hours
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2b720bfd3c8b4882b60c2b5111dafde6
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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