Hydrochloric Acid → 2-(2-Bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione

HRID 2280723Notes

Reaction equation

HRID 2280723 reaction equation
[CH:1]1([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:6][CH2:5]CC=[CH:2]1.[Br:18]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.Cl.[CH2:31]([OH:33])[CH3:32]>C1COCC1>[Br:18][CH:2]1[CH:31]([OH:33])[CH2:32][CH2:5][CH2:6][CH:1]1[N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 105854002-(Cyclohex-2-enyl)isoindoline-1,3-dione

Product 1

HCID 143399982-(2-Bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Cyclohex-2-enyl-isoindole-1,3-dione (520 g, 2.30 mol) and N-bromosuccinimide (416 g, 2.35 mol) were mixed in a cosolvent of chloroform (3000 mL) and ethanol (120 mL) and stirred at room temperature for 16 h. When HPLC showed the starting material was consumed, the reaction mixture was concentrated to give the residue, which was diluted with hydrochloride solution (450 mL, 2.0 mol) and THF (2000 mL), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated to give the crude product. The crude product was washed with ethanol (2 times) to give 2-(2-bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione (400 g, 1.23 mol) as a white solid. 1H NMR (CD3OD, 400 MHz): δ ppm 7.87 (m, 4H), 4.70 (m, 1H), 4.33 (m, 1H), 3.70 (m, 1H), 2.15 (m, 2H), 1.88 (m, 2H), 1.53 (m, 2H).

Workup

  1. customwas consumed
  2. concentrationthe reaction mixture was concentrated
  3. customto give the residue, which
  4. stirringthe reaction mixture was stirred at room temperature for 2 h
  5. concentrationThe reaction mixture was concentrated
  6. customto give the crude product
  7. washThe crude product was washed with ethanol (2 times)

Sources & evidence

ORD record
ord-c334c723946b4227a10649f6d92c8e25
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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