Hydrochloric Acid → HCID 59626035, compound

HRID 401640Notes

Reaction equation

HRID 401640 reaction equation
[Cl:1][C:2]1[C:3]2[CH:14]=[C:13]([F:15])[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9]C)=[O:8].[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[C:3]2[CH:14]=[C:13]([F:15])[C:12]([C:16]([F:17])([F:19])[F:18])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59626047HCID 59626047, compound

Product 1

HCID 59626035HCID 59626035, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-chloro-5-fluoro-6-trifluoromethyl-benzo[b]thiophene-2-carboxylate 10d (180 mg, 0.58 mmol) was stirred with LiOH (55 mg, 2.3 mmol) in THF (5 mL) and H2O (2.5 mL) for 4 h. Aqueous 1N HCl solution was added to the mixture to adjust pH to 3˜4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 10f (150 mg).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. washThe organic solution was washed with aq. NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cd51691aec04120ade5725c94b3c6fa
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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