Trifluoroacetic acid → 6-Acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276913Notes

Reaction equation

HRID 276913 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].ClC1C=CC=[C:22]([C:26]([O:28]O)=[O:27])C=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:26]([O:28][C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:18])[C:6]3([CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH2:17][CH2:16][CH2:15][C:13]=1[C:14]=23)(=[O:27])[CH3:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 226295546-Acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 ml portion of methylene chloride solution of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (94 mg, 0.26 mmol) was cooled to 0° C. and then mixed with 93 mg (0.52 mmol) of m-chloroperbenzoic acid and 21 μl (0.26 mmol) of trifluoroacetic acid. After 2 hours of stirring in the dark at a room temperature, the reaction solution was extracted with chloroform and washed with sodium sulfite and sodium bicarbonate in that order. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (20 cc; elution with ethyl acetate-hexane=1:2) to obtain 88 mg of the title compound (89% in yield).

Workup

  1. extractionthe reaction solution was extracted with chloroform
  2. washwashed with sodium sulfite and sodium bicarbonate in that order
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe thus obtained oily substance was purified by a silica gel column chromatography (20 cc; elution with ethyl acetate-hexane=1:2)

Sources & evidence

ORD record
ord-51cc4d8984ee4b2a978ae7075eee8f4e
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

Loading…