Dimethylformamide → HCID 18467013, compound

HRID 2277106Notes

Reaction equation

HRID 2277106 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1C=O.[C:11](=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:22]([O:24][C:25](=[O:28])[CH2:26][SH:27])[CH3:23]>O>[CH2:22]([O:24][C:25]([C:26]1[S:27][C:3]2[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:2]=2[CH:11]=1)=[O:28])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 18467013HCID 18467013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2,5-difluorobenzaldehyde (280 g, 1.97 mol), potassium carbonate (272 g, 1.97 mol) and anhydrous DMF (1260 ml) was added mercaptoacetic acid ethyl ester (236 g, 1.97 mol). The mixture was stirred at 90° C. for 4 h. After cooling water (4200 ml) was added and the solution was extracted with ethyl acetate (3×1500 ml), the combined extracts dried over sodium sulfate and the solvent was removed to give crude product, which was flash-chromatographed (eluent-ethyl acetate (1):hexane (9). Yield of 6-fluoro-benzo[b]thiophene-2-carboxylic acid ethyl ester 96.49 g (21.8%) as a yellow solid. 1H-NMR (400 MHz, CDCl3); δ (ppm): 1.40 (t, 3H), 4.40 (q, 2H), 7.15 (t, 1H), 7.52 (d, 1H), 7.81 (dd, 1H), 8.00 (s, 1H).

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate (3×1500 ml)
  3. dry with materialthe combined extracts dried over sodium sulfate
  4. customthe solvent was removed
  5. customto give crude product, which
  6. customwas flash-chromatographed (eluent-ethyl acetate (1)

Sources & evidence

ORD record
ord-e2c478e1f5544c88b7dd79736bb80be1
Source dataset
uspto-grants-2015_09
Patent number
US09133159B2

Reaction notes

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