Calcium Carbonate → Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 5-amino-4-bromo-

HRID 894625Notes

Reaction equation

HRID 894625 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3.C(=O)([O-])[O-].[Ca+2].[Br:19]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[C:3]=1[Br:19])[CH2:9][CH2:8]3

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 24408BromineHCID 12925991HCID 12925991, compound

Product 1

HCID 3055477Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 5-amino-4-bromo-

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-17 °C

Procedure

5-Aminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (0.747 g.) and calcium carbonate (0.47 g.) were suspended in a mixture of carbon tetrachloride (20 ml.) and methylene chloride (5 ml.). The suspension was cooled to -17° C., then bromine (0.22 ml.) was added thereto dropwise, followed by stirring for 45 minutes. The reaction mixture was poured into ice-water, then extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated off, and the residue was recrystallized from ethanol-water. By the above procedure there was obtained 5-amino-4-bromospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one as yellow needles melting at 167°-170° C. Yield 0.6 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customThe solvent was evaporated off
  5. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-e6844d638f9a4e05aa72564fcbfd7946
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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