Dimethyl Sulfoxide → HCID 58464908, compound

HRID 1185362Notes

Reaction equation

HRID 1185362 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([B:8]([OH:10])[OH:9])[CH:7]=1.[CH3:13][N:14]([CH2:19][C:20](O)=[O:21])[CH2:15][C:16](O)=[O:17].C1(C)C=CC=CC=1.CS(C)=O>O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([B:8]2[O:10][C:20](=[O:21])[CH2:19][N:14]([CH3:13])[CH2:15][C:16](=[O:17])[O:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 20441N-methyliminodiacetic acidHCID 44558191(5-Bromo-2-fluoro-3-methylphenyl)boronic acid

Product 1

HCID 58464908HCID 58464908, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL round bottom flask equipped with a stir bar was added 5-bromo-2-fluoro-3-methylphenylboronic acid (1.0 g, 4.3 mmol), N-methyliminodiacetic acid (0.76 g, 5.2 mmol), toluene (8 mL) and DMSO (2 mL). The flask was fitted with a Dean-Stark trap and the Dean-Stark trap was fitted with a reflux condenser. The mixture was heated to reflux with azeotropic removal of water for 4.5 h. The solution was concentrated in vacuo. The residue was absorbed on Celite in vacuo from an acetone suspension and the resulting powder was subjected to Isco flash chromatography eluted with 0 to 70% acetonitrile in ether to give 2-(5-bromo-2-fluoro-3-methylphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (1.26 g, 86%).

Workup

  1. customTo a 50 mL round bottom flask equipped with a stir bar
  2. customThe flask was fitted with a Dean-Stark trap
  3. customthe Dean-Stark trap was fitted with a reflux condenser
  4. temperatureThe mixture was heated
  5. concentrationThe solution was concentrated in vacuo
  6. customThe residue was absorbed on Celite in vacuo from an acetone suspension
  7. washeluted with 0 to 70% acetonitrile in ether

Sources & evidence

ORD record
ord-0df683815a644fe68c0e7e22b1f121f1
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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