Hydrochloric Acid → HCID 67210852, compound

HRID 1877657Notes

Reaction equation

HRID 1877657 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:11]=3[C:12]=2[C:13]([O-:15])=[O:14])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:11]=3[C:12]=2[C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178524035HCID 178524035, compound

Product 1

HCID 67210852HCID 67210852, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-(4-fluorophenyl)-5-hydroxybenzofuran-3-carboxylate (1 g, 3.5 mmol, 1 eq) in a 1:1 mixture of MeOH/THF at ambient temperature was added 5 eq. of NaOH and heated to 60° C. for 3 h. The mixture was cooled to ambient temperature and to 0° C. in an ice-water bath, it was acidified slowly with 1.5 N HCl and then concentrated. The mixture with white precipitates was diluted with water and filtered to get the solid. It is further washed with water and dried in vacuum. Yield: 0.9 g (94.6%). 1H NMR (400 MHz, DMSO-d6): δ 6.82-6.85 (m, 1H), 7.35-7.40 (m, 3H), 7.46-7.49 (d, 1H, J=8.84 Hz), 8.02-8.05 (m, 2H), 9.4 (s, 1H), 13.05 (s, 1H). LCMS: (ES−) m/z=271.1

Workup

  1. temperatureThe mixture was cooled to ambient temperature and to 0° C. in an ice-water bath
  2. concentrationconcentrated
  3. customThe mixture with white precipitates
  4. additionwas diluted with water
  5. filtrationfiltered
  6. customto get the solid
  7. washIt is further washed with water
  8. customdried in vacuum

Sources & evidence

ORD record
ord-62d4a68a329d41659bf2edf8f5608e05
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

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