Hydrochloric Acid → HCID 67210852, compound

HRID 555159Notes

Reaction equation

HRID 555159 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-0490839ca6a14ebbbb64a93ff6ea06d9
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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