Acetonitrile → (R)-4-(5-bromo-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 1036476Notes

Reaction equation

HRID 1036476 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.C(#N)C.[Br:22]N1C(=O)CCC1=O>>[Br:22][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)=[CH:8]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67413226(R)-4-(5-bromo-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneYield 82%

Conditions

Temperature
0 °C

Procedure

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (Example 4, 5.05 g, 20.8 mmol) was suspended in acetonitrile (50 mL, 1000 mmol) in a capped 200 mL round-bottom flask equipped with a magnetic stir bar. The mixture was cooled to 0° C. and N-bromosuccinimide (3.88 g, 21.8 mmol) was added. The reaction mixture was stirred for 1 hour. HPLC analysis indicated that the reaction was complete. The mixture was filtered. The residue was rinsed with acetonitrile, air dried under vacuum and collected (5.54 g). The crude product required no purification (82% yield).

Workup

  1. customequipped with a magnetic stir bar
  2. filtrationThe mixture was filtered
  3. washThe residue was rinsed with acetonitrile, air
  4. customdried under vacuum
  5. customcollected (5.54 g)
  6. customno purification (82% yield)

Sources & evidence

ORD record
ord-c76006280b22436cbad1db7c0958ac8e
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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