Hydrochloric Acid → [1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid

HRID 1373871Notes

Reaction equation

HRID 1373871 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:13]=2)[C:8]=1[Br:35])C.[OH-].[K+].Cl>C1COCC1.O>[Br:35][C:8]1[C:9]2[C:14](=[CH:13][C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:36])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69410855[1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Product 1

HCID 11237897[1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acidYield 24.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.427 g, 0.764 mmol) and potassium hydroxide (0.162 g 2.89 mmol) in THF (125 mL) and water (125 mL) was stirred at ambient temperature for two hours. It was then poured in excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, solvent evaporated and purified by HPLC using 65% acetonitrile (0.1% trifluoroacetic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for 25 minutes to yield [1-bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a yellow solid (0.100 g, 24.6%): MP: 170–2° C.; mass spectrum (+EI, [M+H]+) m/z 531/533. 1H NMR (500 MHz, DMSO-d6): δ13.0–13.3 (br, 1H), 8.27 (d, 1H, J=8.86 Hz), 8.16 (d, 1H, J=1.52 Hz), 8.06–8.12 (m, 2H), 7.89–7.92 (m, 1H), 7.81 (dd, 1H, J=8.86 Hz and 1.83 Hz), 7.44–7.52 (m, 3H), 7.13–7.19 (m, 3H), 6.92–6.94 (m, 2H), 5.02 (s, 2H), 3.81 ppm (s, 2H).

Workup

  1. extractionThis was then extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. custompurified by HPLC
  7. customEvaporating the solvent
  8. extractionextracting with ethyl acetate
  9. washwashing with water and brine
  10. dry with materialdrying with anhydrous magnesium sulfate
  11. filtrationfiltering
  12. concentrationconcentrating
  13. customdrying in vacuo at 60° C. for 25 minutes

Sources & evidence

ORD record
ord-c667beb5a41d421e9000710fe2eee57f
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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