Sodium Hydroxide → HCID 89155066, compound

HRID 1405196Notes

Reaction equation

HRID 1405196 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH2:11][S:12]([CH3:15])(=[O:14])=[O:13].[OH-].[Na+]>Cl.C1COCC1.[Cl-].[Cl-].[Ti+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH2:11][S:12]([CH3:15])(=[O:14])=[O:13]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 70976451HCID 70976451, compound

Product 1

HCID 89155066HCID 89155066, compoundYield 116.9%

Reagents, catalysts & solvents 3

HCID 10290777Titanium(2+);dichlorideCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of titanous chloride (about 15%) in about 10% hydrochloric acid (MERCK (MDA) INCL SCHUCHARDT, 71.5 mL) was added to a stirred solution of 1-fluoro-2-[(methylsulfonyl)methyl]-4-nitrobenzene (1.61 g) in THF (80 mL) at room temperature and stirred for 16 hours. By adding 1N sodium hydroxide solution the pH value of the reaction mixture was raised to 10 before it was extracted with ethyl acetate (2×). The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to give the crude title compound (1.64 g) which crystallized from diethylether/Ethyl acetate (1.16 g).

Workup

  1. temperaturewas raised to 10 before it
  2. extractionwas extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d594f12053994633a5240dbbf9c9d4c1
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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