Hydrochloric Acid → 5-Bromoisoindoline

HRID 1927700Notes

Reaction equation

HRID 1927700 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=O)[NH:12][C:11]2=O.CO.Cl>C1COCC1.O>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][NH:12][CH2:11]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2360184-BromophthalimideHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 147958715-Bromoisoindoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

564.2 ml of a 1M borane/THF solution are added dropwise to 42.5 g (188 mmol) of 5-bromoisoindole-1,3-dione in 300 ml of THF (dry) at −5° C. over a period of 60 min. The mixture is subsequently stirred for 2 h at 22° C. and then for 16 h at 80° C. The mixture is then cooled to 0° C., before 200 ml of methanol (exothermic!) and 200 ml of 2M hydrochloric acid are slowly added. The resultant mixture is stirred for 3 h at 80° C., cooled to 22° C., and 100 ml of water are added. The aqueous solution is extracted three times with 150 ml of dichloromethane each time, dried over sodium sulfate, filtered and evaporated to dryness: 5-bromo-2,3-dihydro-1H-isoindole; yield 15.4 g of “13” (41.3%); MW 198.06; Rt 1.099 min (“polar” method).

Workup

  1. waitfor 16 h at 80° C
  2. additionare slowly added
  3. temperaturecooled to 22° C.
  4. extractionThe aqueous solution is extracted three times with 150 ml of dichloromethane each time
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d229a22a1ecd4fe085383083a2763e1e
Source dataset
uspto-grants-2012_05
Patent number
US08183279B2

Reaction notes

Loading…