Sulfuric Acid → HCID 86640659, compound

HRID 558120Notes

Reaction equation

HRID 558120 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](O)([CH3:16])[CH3:15].C[Si]([C:22]#[N:23])(C)C.[OH-:24].[NH4+]>>[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]([NH:23][CH:22]=[O:24])([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 82115Trimethylsilyl cyanideHCID 23233808HCID 23233808, compound

Product 1

HCID 86640659HCID 86640659, compoundYield 75%

Procedure

Add 98% sulfuric acid drop-wise (3 g, 31 mmol) to a mixture of 2-(2-bromo-4-fluoro-phenyl)-propan-2-ol (2.4 g, 10.30 mmol) and trimethylsilyl cyanide (2.04 g, 59 mmol) in a 25-mL round bottom flask under N2 at −20° C. Move the flask out of the cooling bath and stir the mixture at RT overnight. Dilute the mixture with ice-water and neutralize with ammonium hydroxide to pH=8. Extract the product with chloroform/IPA (3/1, 100 mL). Wash the organic phase with water/aqueous saturated sodium chloride, dry over sodium sulfate, and concentrate in vacuo to give the crude product. Purify by FCC (20% THF in DCM as elute) to give the title compound as a white solid (2 g, 75%). MS (ES) m/z 260/262 [M+1]+.

Workup

  1. extractionExtract the product with chloroform/IPA (3/1, 100 mL)
  2. washWash the organic phase with water/aqueous saturated sodium chloride
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customto give the crude product
  6. customPurify by FCC (20% THF in DCM as elute)

Sources & evidence

ORD record
ord-c673b1225ead48e0949adc8c6830e9c0
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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