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

HRID 2057954Notes

Reaction equation

HRID 2057954 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>>[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

3

Reactant 2

HCID 6885PhthalideHCID 67184N-bromobutanimide

Product 1

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

Procedure

A benzoic acid derivative of formula 1 is reacted with formaldehyde under acidic conditions to yield a phthalide derivative of formula 2. ##STR4## The phthalide derivative is then brominated with any suitable brominating agent, e.g. N-bromosuccinimide to yield an unstable bromophthalide derivative, 3, which is readily reacted with water to a phthalaldehydic acid derivative, 4. ##STR5## The phthalaldehydic acid derivative may then be oxidized to the desired phthalic anhydride derivative, 5, in good yield using a suitable oxidizing agent such as manganese dioxide. ##STR6##

Sources & evidence

ORD record
ord-c4eb36781187455e8ca246a0f5f2246e
Source dataset
uspto-grants-1980_07
Patent number
US04213996

Reaction notes

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