Acetonitrile → HCID 86700525, compound

HRID 625188Notes

Reaction equation

HRID 625188 reaction equation
Br[C:2]([F:20])([F:19])[C:3]([CH:6]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH:7]1[C:15]([O:17][CH3:18])=[O:16])([F:5])[F:4].C(=O)(O)[O-].[Na+:25].[S:26](S([O-])=O)([O-:28])=[O:27].[Na+].[Na+].C(#N)C>O>[CH3:18][O:17][C:15]([CH:7]1[CH2:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH:6]1[C:3]([F:5])([F:4])[C:2]([F:20])([F:19])[S:26]([O-:28])=[O:27])=[O:16].[Na+:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 86700527HCID 86700527, compound

Product 1

HCID 86700525HCID 86700525, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a glass flask equipped with a thermometer and a capacitor were charged 2.00 g (5.49 mmol) of dimethyl 4-(2-bromo-1,1,2,2-tetrafluoroethyl)cyclopentane-1,3-dicarboxylate, 0.920 g (11.0 mmol) of sodium bicarbonate, 1.62 g (9.30 mmol) of sodium dithionite, 15 mL of acetonitrile and 15 mL of water, and the mixture was stirred at 50° C. for 8 hrs. The disappearance of the raw material was confirmed by 19F-NMR to decide completion of the reaction. Thereafter, acetonitrile was distilled off in vacuo to obtain an aqueous solution of crude sodium 2-(2,4-bis(methoxycarbonyl)cyclopentyl)-1,1,2,2-tetrafluoroethanesulfinate (precursor compound (a-4)) represented by the following formula (a-4) without carrying out further purification, which was used for the following reaction.

Workup

  1. customInto a glass flask equipped with a thermometer
  2. customcompletion of the reaction
  3. distillationThereafter, acetonitrile was distilled off in vacuo

Sources & evidence

ORD record
ord-18f4893877f14d0b95901dc005c8da77
Source dataset
uspto-grants-2016_04
Patent number
US09304393B2

Reaction notes

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