Dimethyl Sulfoxide → HCID 58464908, compound

HRID 2089405Notes

Reaction equation

HRID 2089405 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-19b9b466d2bb46d5a70e9588cd2e1ddb
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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