1,2-Dichloroethane → HCID 87231630, compound

HRID 558161Notes

Reaction equation

HRID 558161 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH:11]=O.Cl[CH2:19]CCl>O>[Br:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1/[C:11](=[N:7]/[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])/[CH3:19]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 87231630HCID 87231630, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add (S)-(−)-2-methyl-2-propanesulfinamide (15 g, 73.89 mmol) to a stirring mixture of 2-bromo-4-fluorobenzaldehyde (9.85 g, 81.28 mmol) in 1,2-dichloroethane (50 mL) at RT. And then add Ti(OEt)4 (25.28 g, 4.78 mol) to the mixture and stir overnight at RT. Cool the reaction in an ice/water bath, and dilute with water. Filter the reaction mixture over a ½ inch pad of celite, and wash the filtered stuff with dichloromethane (4×150 mL). Separate the organic layer and wash the aqueous layer with 150 mL DCM. Combine the organic layers, dry over MgSO4, filter, and concentrate. Purify the residue via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate. Pool the desired fractions and concentrate to give the product as a very pale yellow oil (21.5 g, 95%). GCMS m/z 305 [M]+.

Workup

  1. temperatureCool
  2. customthe reaction in an ice/water bath
  3. filtrationFilter the reaction mixture over a ½ inch pad of celite
  4. washwash the filtered stuff with dichloromethane (4×150 mL)
  5. customSeparate the organic layer
  6. washwash the aqueous layer with 150 mL DCM
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify the residue via silica chromatography
  11. washeluting with hexanes to 8:2 hexanes
  12. concentrationPool the desired fractions and concentrate

Sources & evidence

ORD record
ord-0f12c22812a148ba89a1bccb8b167528
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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