Hydrochloric Acid → {1-Bromo-6-[3-(3,3-dimethyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid

HRID 1373875Notes

Reaction equation

HRID 1373875 reaction equation
C([O:3][C:4](=[O:34])[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:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:13]=2)[C:8]=1[Br:33])C.[OH-].[K+].Cl>C1COCC1.O>[Br:33][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:32])[CH2:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:34])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69411486{1-Bromo-6-[3-(3,3-dimethyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid ethyl ester

Product 1

HCID 21075896{1-Bromo-6-[3-(3,3-dimethyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acidYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {1-bromo-6-[3-(3,3-dimethyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid ethyl ester (0.360 g, 0.667 mmol) and potassium hydroxide (0.125 g, 2.23 mmol) in THF (5 mL) and water (5 mL) was stirred at ambient temperature for four 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 dried in vacuo at 78° C. for 12 hours to yield {1-bromo-6-[3-(3,3-dimethyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid as a light yellow solid (0.233 g, 68.3%): MP: 206–7° C.; mass spectrum (+EI, [M+H]+) m/z 511/513. 1H NMR (500 MHz, DMSO-d6): δ12.9–13.4 (br, 1H), 8.24 (d, 1H, J=9.01 Hz), 8.11–8.13(m, 2H), 8.07–8.09 (m, 1H), 7.74 (dd, 1H, J=8.78 Hz and 1.76 Hz), 7.46–7.51 (m, 3H), 5.02 (s, 2H), 2.33 (s, 2H), 0.76 ppm (s, 9H). Elemental Analysis for C26H23BrNO4S: Calcd: C, 61.06; H, 4.53; N, 0.00; Found: C, 61.17; H,4.64; N, 0.00.

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. customdried in vacuo at 78° C. for 12 hours

Sources & evidence

ORD record
ord-02a45c7a6d3b44d9994915a872dacbfd
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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