Ethyl bromoacetate → HCID 45104337, compound

HRID 2385020Notes

Reaction equation

HRID 2385020 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.O>[F:1][C:2]1[C:3]2[O:10][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][C:4]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 45104337HCID 45104337, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoro-2-hydroxybenzaldehyde (5.00 g, 35.7 mmol), potassium carbonate (9.85 g, 71.4 mmol), and ethyl bromoacetate (4.30 ml, 39.3 mmol) in N,N-dimethylformamide (70 mL) was heated at 100° C. for 16 h. The mixture was diluted with water (500 mL) and extracted with ethyl acetate (3×150 mL). The combined organic solution was washed with brine (150 mL), dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo. The residue was purified by column chromatography (hexanes/ethyl acetate, 49/1→9/1) to afford ethyl 7-fluorobenzofuran-2-carboxylate (3.86 g, 52%) as a yellowish oil: 1H NMR (300 MHz, CDCl3) δ7.56-7.54 (m, 1H), 7.47-7.42 (m, 1H), 7.28-7.14 (m, 2H), 4.46 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe combined organic solution was washed with brine (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (hexanes/ethyl acetate, 49/1→9/1)

Sources & evidence

ORD record
ord-75bbd86606444be999102fce53300923
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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