Hydrochloric Acid → HCID 86587877, compound

HRID 1006277Notes

Reaction equation

HRID 1006277 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C(N(CC)CC)C.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[OH:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1/[CH:14]=[CH:13]/[C:12]([O:16][CH2:17][CH3:18])=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 81672542-Bromo-3-nitrophenol

Product 1

HCID 86587877HCID 86587877, compoundYield 517%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a thick-walled vessel was charged with 2-bromo-3-nitrophenol (1.16 g, 5.32 mmol), ethyl acrylate (666 mg, 0.72 mmol), tri-(o-tolyl)phosphine (65 mg, 0.21 mmol), palladium acetate (12 mg, 0.05 mmol), and triethylamine(10 mL). The vessel was then sealed and the resulting mixture was heated to 100° C. overnight. In the morning, the vessel was cooled to rt and the mixture was poured into water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The residue was purified with silica gel flash chromatography by using hexane/ethyl acetate (2/1) as the eluant to give ethyl (2E)-3-(2-hydroxy-6-nitrophenyl)prop-2-enoate (883 mg, 70%): Rf0.16 (3/1 hexane/ethyl acetate); 1H NMR (CDCl3) δ 7.6(d, J=16.1 Hz, 1H), 7.05-7.23 (m, 3H), 6.71 (dd, J=16.1, 0.8 Hz, 1H), 4.18 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 2H).

Workup

  1. customThe vessel was then sealed
  2. temperatureIn the morning, the vessel was cooled to rt
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified with silica gel flash chromatography

Sources & evidence

ORD record
ord-5d4c27fafdaf4705929f6dd143fad4e7
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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