Carbon Tetrachloride → HCID 19906403, compound

HRID 2371789Notes

Reaction equation

HRID 2371789 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][C:17]3=[O:20])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:21]Br.C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>Cl.C(Cl)Cl>[Br:21][CH:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][C:10]([NH:9][C:7](=[O:8])[CH2:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:11][CH:12]=2)[C:17]1=[O:20]

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8857Ethyl AcetateHCID 24408BromineHCID 19906358HCID 19906358, compound

Product 1

HCID 19906403HCID 19906403, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-cyclopentylacetamido-1-tetralone (1.02 g) in ethereal HCl (0.2 ml) and methylene chloride (20 ml) was added a solution of bromine (0.19 ml) in a mixture of ethereal HCl (10 drops) and carbon tetrachloride (1 ml). The reaction was stirred for 3 h and ethyl acetate (60 ml) was added. The mixture was washed (saturated sodium bicarbonate, water, brine), dried (MgSO4), and evaporated. The residue was recrystallized from methylene chloride and petroleum ether to give 2-bromo-7-cyclopentylacetamido-1-tetralone (1.23 g, 95%) as a colorless solid; mp 162.5°-164.0° C.

Workup

  1. washThe mixture was washed (saturated sodium bicarbonate, water, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was recrystallized from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-103319f4806b4f6a812c3e0791349a5e
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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