Phosphorus tribromide → (R)-2-(1-bromopropan-2-yl)isoindoline-1,3-dione

HRID 872466Notes

Reaction equation

HRID 872466 reaction equation
O[CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].P(Br)(Br)[Br:17]>>[Br:17][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4]

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 6418462-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 2733602(R)-2-(1-bromopropan-2-yl)isoindoline-1,3-dioneYield 142.8%

Procedure

(R)-2-(1-hydroxypropan-2-yl)isoindoline-1,3-dione (8.75 g, 43 mmol) and phosphorus tribromide (2.73 ml. 29 mmol) were heated at 175° C. for 50 min. To cooled reaction mixture was added ice (50 ml). Thus formed precipitate was filtered, washed with water and dried under vacuum to obtain 11.1 g (97%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.50 (d, 3H), 3.85 (m, 1H), 4.01 (m, 1H), 4.49 (m, 1H), 7.88 (m, 4H).

Workup

  1. temperatureTo cooled
  2. customreaction mixture
  3. filtrationThus formed precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2d67e0caf1f4416aa7f3e3e499dec02f
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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