Bromine → 849630-82-6

HRID 268685Notes

Reaction equation

HRID 268685 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]2=[O:14])([CH3:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[Br:15][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1)[NH:11][C:10](=[O:13])[C:9]2=[O:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 122727937-Isopropylindoline-2,3-dione

Product 1

HCID 39082924849630-82-6Yield 98.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
75 °C

Procedure

7-isopropylindoline-2,3-dione (23.8 g, 0.12 mol) was added to a stirred solution of glacial acetic acid (700 ml). To this solution was added, via additional funnel bromine (7.8 ml, 0.15 mol) in glacial acetic acid (300 ml) during 30 min. After the addition, the combined mixture was stirred at 75° C. for 3 hr, cooled, and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, and evaporated in vacuo; air dried to give (31.8 g, 94%) of crude product. 1H NMR (300 MHz, CDCl3) δ 8.04 (b, NH), 7.59 (dd 2H), 2.84 (m, 1H), 1.31 (d, 6H); ESI (+) MS m/e=269 (MH+), ESI (−) MS m/e=267 (MH−).

Workup

  1. additionAfter the addition
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customair dried

Sources & evidence

ORD record
ord-d0b2e1e40f244db09d5cff7d7ff21480
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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