Methanol → HCID 86723244, compound

HRID 1846022Notes

Reaction equation

HRID 1846022 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1F.[OH2:16].C(Cl)Cl.[CH3:20]O>>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][C:4]=1[O:16][CH3:20]

Participants

6

Reactant 5

HCID 887Methanol2×HCID 962WaterHCID 6344DichloromethaneHCID 5360545SodiumHCID 86723245HCID 86723245, compound

Product 1

HCID 86723244HCID 86723244, compoundYield 73%

Procedure

Sodium (95 mg, 4.12 mmol) was added portionwise to MeOH (2 mL). After stirring at room temperature for 1 hour, this solution was added dropwise to a suspension of 1-bromo-4-(cyclopropylsulfonyl)-2-fluorobenzene (Preparation 32, 115 mg, 0.41 mmol) in MeOH (2 mL), and the resulting mixture stirred at 60° C. for 16 hours. After cooling to room temperature, water (10 mL) and CH2Cl2 (10 mL) were added, and the resulting mixture partitioned. The aqueous was extracted with CH2Cl2 (2×10 mL), and the combined organic layers washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography eluting with heptanes/CH2Cl2 1:2 afforded the title compound as a colourless solid in 73% yield, 88 mg.

Workup

  1. stirringthe resulting mixture stirred at 60° C. for 16 hours
  2. temperatureAfter cooling to room temperature
  3. customthe resulting mixture partitioned
  4. extractionThe aqueous was extracted with CH2Cl2 (2×10 mL)
  5. washthe combined organic layers washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel column chromatography
  9. washeluting with heptanes/CH2Cl2 1:2

Sources & evidence

ORD record
ord-bb189fec5b634715a7bb4c6b917e4781
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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