Hydrochloric Acid → 5-Bromo-1H-indene-1,3(2H)-dione

HRID 1288601Notes

Reaction equation

HRID 1288601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[CH2:13](N(CC)CC)C.C(OCC)(=O)CC(C)=O.Cl>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[CH2:13][C:9]2=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 665904-Bromophthalic anhydride

Product 1

HCID 108788305-Bromo-1H-indene-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-bromo phthalic anhydride (4.15 g; 0.018 mole) in acetic anhydride (10 g) containing triethylamine (4 g) was treated at room temperature with ethyl acetoacetate (2.38 g; 0.02 mole). After 24 hrs. with stirring, crushed ice (20 g) and concentrated hydrochloric acid (10 ml) were added and the precipitated red solid filtered. Addition of a hot (70°-80° C) solution of hydrochloric acid (150 ml) in water (750 ml) to this solid resulted in decarboxylation and generation of 5-bromo indane-1,3-dione as red plates, m.p. (acetone) 152°-3° C. (Found; C, 48.04; H, 2.17; Br, 35.63; C9H5Br O2 requires C, 48.05; H, 2.24; Br, 35.52%).

Workup

  1. additionwere added
  2. filtrationthe precipitated red solid filtered
  3. additionAddition of a hot (70°-80° C) solution of hydrochloric acid (150 ml) in water (750 ml) to this solid

Sources & evidence

ORD record
ord-53b5dcf78c7242b6a499fa72671f7845
Source dataset
uspto-grants-1976_10
Patent number
US03988476

Reaction notes

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