Ethyl bromoacetate → HCID 69411210, compound

HRID 1373879Notes

Reaction equation

HRID 1373879 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12]([Cl:16])=[C:11]([OH:17])[CH:10]=[CH:9]3)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CC(C)=O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][O:17][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([C:5]3[S:1][C:2]4[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=4[CH:4]=3)[CH:7]=2)[C:12]=1[Cl:16])[CH3:34]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 21075903HCID 21075903, compound

Product 1

HCID 69411210HCID 69411210, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol (3.19 g, 10.2 mmol) and cesium carbonate (6.8 g, 21 mmol) in acetone (100 mL) was stirred at ambient temperature for one hour and 15 minutes. Ethyl bromoacetate (1.4 mL, 12 mmol) was added, and the reaction mixture was stirred for 3.5 hours at ambient temperature. The insoluble solids were then filtered, and the filtrate was solvent evaporated. The residue was dissolved in hot chloroform and washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was then stirred in hexane for about ten minutes and filtered and rinsed with hexane. Drying at 65° C. in vacuo for two hours yielded (6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-yloxy)-acetic acid ethyl ester as a light yellow solid (2.7 g, 67%): MP: 187–8° C.; Mass spectrum (+ES, [M+H]+) m/z 397/399. 1HNMR (500 MHz, DMSO-d6): δ8.34 (d, 1H, J=1.68 Hz), 8.21 (d, 1H, J=8.85 Hz), 8.13 (dd, 1H, J=8.93 and 1.76 Hz), 8.01–8.07 (m, 3H), 7.89–7.90 (m, 1H), 7.52 (d, 1H, J=9.15 Hz), 7.37–7.44 (m, 2H), 5.11 (s, 2H), 4.20 (q, 2H, J=7.12 Hz), 1.23 ppm (t, 3H, J=7.10 Hz). Elemental Analysis for C22H17ClO3S: Calcd: C, 66.58; H, 4.32; N, 0.00; Found: C, 66.43; H, 4.27; N, 0.00.

Workup

  1. stirringthe reaction mixture was stirred for 3.5 hours at ambient temperature
  2. filtrationThe insoluble solids were then filtered
  3. customevaporated
  4. dissolutionThe residue was dissolved in hot chloroform
  5. washwashed with water and brine
  6. dry with materialIt was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customsolvent evaporated
  9. stirringThe residue was then stirred in hexane for about ten minutes
  10. filtrationfiltered
  11. washrinsed with hexane
  12. customDrying at 65° C. in vacuo for two hours

Sources & evidence

ORD record
ord-fc0831ce40764f57b36116c8d313512e
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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