Hydrochloric Acid → HCID 67211105, compound

HRID 1877650Notes

Reaction equation

HRID 1877650 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:18]([O:20]CC)=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:23].C1COCC1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[C:7]2[C:8]([C:18]([OH:20])=[O:19])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66634105HCID 66634105, compound

Product 1

HCID 67211105HCID 67211105, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixyure of ethyl 4-fluoro-2-(4-fluorophenyl)-5-hydroxybenzofuran-3-carboxylate (108.9 mg, 0.342 mmol) in a mixture of MeOH (2 mL)/THF (2 mL) at r.t. under N2 was added sodium hydroxide (1.0 mL, 1.0 mmol) (1 M aq.). The mixture was stirred at 100° C. for 1.5 hours. The mixture was cooled to r.t., added with 1.5 ml 1N HCl, and then added 10 ml H2O. The white precipitates were filtered and washed with 3×2 ml H2O and dried (73 mg). 1H NMR (500 MHz, CD3OD) δ 7.98 (m, 2H), 7.25 (t overlapping with dd, 2H), 7.24 (dd, 1H), 7.02 (t, J=8.39, 1H). LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=5 ml/min, Column: Phenomenex-Luna, 3.0×50 mm, S10; (ES+) m/z (M+H)+=291.01, HPLC Rt=1.478 min.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. customThe white precipitates
  3. filtrationwere filtered
  4. washwashed with 3×2 ml H2O
  5. customdried (73 mg)
  6. customB=100, Gradient time=2 min
  7. customtime=3 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-062cf6a014c04465b6d64e09dd66b7aa
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

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