Phthalide → 1(3H)-Isobenzofuranone, 3-bromo-

HRID 326060Notes

Reaction equation

HRID 326060 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:2])[O:3]1

Participants

4

Reactant 2

HCID 6885PhthalideHCID 67184N-bromobutanimide

Product 1

HCID 962181(3H)-Isobenzofuranone, 3-bromo-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
15 °C

Procedure

As taught by U.S. Pat. No. 3,860,579, recrystallized phthalide (50 g., 0.375 mol) and recrystallized N-bromosuccinimide (0.375 mol) were refluxed 4.5 hours in the presence of about 100 mgm α-azobutyronitrile in one liter CCl4. The mixture was cooled to about 15° C. and filtered to remove succinimide which was itself washed with about 100 ml. CCl4 and filtered. The combined CCl4 phases were concentrated in vacuo to about 150 ml. giving solid 3-bromophthalide which was collected by filtration, washed with about 50 ml. CCl4 and air-dried to yield 54 g. which weighed 50 g. after recrystallization from boiling cyclohexane, m.p. 84°-86° C. ##STR39##

Workup

  1. filtrationfiltered
  2. customto remove succinimide which
  3. washwashed with about 100 ml
  4. filtrationCCl4 and filtered
  5. concentrationThe combined CCl4 phases were concentrated in vacuo to about 150 ml

Sources & evidence

ORD record
ord-a95a4efbc48a4c9db3be74d728955880
Source dataset
uspto-grants-1984_04
Patent number
US04444687

Reaction notes

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