Water → HCID 23134202, compound

HRID 858641Notes

Reaction equation

HRID 858641 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[OH:10])[CH3:2].C1(=O)O[CH2:14][CH2:13][O:12]1.C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([O:10][CH2:14][CH2:13][OH:12])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 23134202HCID 23134202, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 2-ethyl-4-bromophenol (3.5 g, 17.4 mmol) and ethylene carbonate (3.22 g, 37 mmol) in NMP (60 mL) was added potassium carbonate (5.17 g, 37.4 mmol). The resulting mixture was heated to 125° C. and maintained for 3 h. The reaction was cooled and poured into water (250 mL) and extracted with EtOAc (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (10–20% EtOAc in hexanes) to give the product (3.5 g, 82% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 1.19 (t, J=7.6 Hz, 3 H), 1.89 (brs, 1 H), 2.61 (q, J=7.6 Hz, 2 H), 4.05 (m, 4 H), 6.70 (d, J=8.7 Hz, 1 H), 7.24 (m, 2 H).

Workup

  1. temperaturemaintained for 3 h
  2. temperatureThe reaction was cooled
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (10–20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a07a621d57934e4fac13c754439aac06
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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