Hydrochloric Acid → HCID 21075897, compound

HRID 1373876Notes

Reaction equation

HRID 1373876 reaction equation
C([O:3][C:4](=[O:35])[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]=[C:23]([C:26](=[O:33])[CH2:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[CH:25][C:19]=4[CH:18]=3)[CH:13]=2)[C:8]=1[Br:34])C.[OH-].[K+].Cl>C1COCC1.O>[Br:34][C:8]1[C:9]2[C:14](=[CH:13][C:12]([C:17]3[S:21][C:20]4[CH:22]=[C:23]([C:26](=[O:33])[CH2:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[CH:25][C:19]=4[CH:18]=3)=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:35])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69411478HCID 69411478, compound

Product 1

HCID 21075897HCID 21075897, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {1-bromo-6-[6-(4,4-dimethyl-pentanoyl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid ethyl ester (0.167 g, 0.310 mmol) and potassium hydroxide (0.056 g, 1.0 mmoles) in THF (20 mL) and water (20 mL) was stirred for one hour at ambient temperature. 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 65° C. for 13.5 hours to yield {1-bromo-6-[6-(4,4-dimethyl-pentanoyl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetic acid as a light yellow solid (0.119 g, 74.8%): MP: 246–7° C.; mass spectrum (−EI, [M−H]−) m/z 509/511. −H NMR (500 MHz, DMSO-d6): δ8.74 (s, 1H), 8.40(d, 1H, J=1.68 Hz), 8.21 (d, 1H, J=9.00 Hz), 8.11–8.15 (m, 3H), 7.97–7.98 (m, 2H), 7.48 (d, 1H, J=9.16 Hz), 5.01 (s, 2H), 3.01 (s, 2H), 1.05 ppm (s, 9H). Elemental Analysis for C26H23BrNO4S: Calcd: C, 61.06; H, 4.53; N, 0.00; Found: C, 60.94; H, 4.59; 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 65° C. for 13.5 hours

Sources & evidence

ORD record
ord-ed338da79dfd4a359ff84029b6c67b4a
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

Loading…