Hydrochloric Acid → HCID 53839942, compound

HRID 2395604Notes

Reaction equation

HRID 2395604 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC.C(N(CC)CC)C>[Br:9][C:4]1[CH:3]=[C:2]([CH:12]=[CH:11][C:10]([O:14][CH3:15])=[O:13])[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 11776TriphenylphosphineHCID 1370031,3-Dibromo-5-fluorobenzene

Product 1

HCID 53839942HCID 53839942, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.1 g (0.02 mol) of 1,3-dibromo-5- fluorobenzene (prepared according to A. Cannoni de Degiorgi and E. V. Zappi, Anales asoc. quim. argentina, 1940, 28, 72) (C. A. 34 65933), 2.2 ml (0.025 mol) of methyl acrylate, 10 ml of triethylamine, 0.044 g (0.002 mol) of palladium acetate and 0.208 g (0.0008 mol) of triphenylphosphine is heated for 24 h at 100° C. in a closed vessel with magnetic stirring. Cooling, pouring into 1N HCl, extraction with ether, washing with water, drying over Na2SO4, filtration and evaporation under vacuum are carried out. The residue is purified by chromatography on silica (eluent: 2/1 hexane/ethyl acetate). Yd.: 2.7 g (51%) M.p.=95°-6° C.

Workup

  1. customprepared
  2. temperatureCooling
  3. washwashing with water
  4. dry with materialdrying over Na2SO4, filtration and evaporation under vacuum
  5. customThe residue is purified by chromatography on silica (eluent: 2/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-97a7ac75daf04756a1f1952c1165835e
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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