Sodium Bicarbonate → HCID 86723242, compound

HRID 1846020Notes

Reaction equation

HRID 1846020 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1F.[C:17](=O)(O)[O-:18].[Na+]>CO>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1[O:18][CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545Sodium2×HCID 86723243HCID 86723243, compound

Product 1

HCID 86723242HCID 86723242, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium (235 mg, 10.2 mmol) was added to MeOH (6 mL) under nitrogen and the mixture stirred until all the sodium had reacted. 1-bromo-4-(cyclobutylsulfonyl)-2-fluorobenzene (Preparation 28, 300 mg, 1.02 mmol) was added and the mixture stirred at 60° C. for 10 hours. 2% aqueous sodium bicarbonate (36 mL) was added and the mixture extracted with EtOAc (2×36 mL), the organic layers dried over sodium sulphate and then concentrated in vacuo. The resulting residue was purified by silica gel column chromatography eluting with CH2Cl2/EtOAc 3:1 to provide the title compound as a white solid 87% yield, 270 mg.

Workup

  1. customhad reacted
  2. extractionthe mixture extracted with EtOAc (2×36 mL)
  3. dry with materialthe organic layers dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washeluting with CH2Cl2/EtOAc 3:1

Sources & evidence

ORD record
ord-834cd8d831fb49e3abf2913b5ed05f58
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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