Benzoyl Peroxide → HCID 15491033, compound

HRID 362871Notes

Reaction equation

HRID 362871 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:15])[CH2:7][CH:8]2[CH2:11][C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl.C1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:15])[CH2:7]/[C:8]/2=[CH:11]\[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23293655HCID 23293655, compound

Product 1

HCID 15491033HCID 15491033, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(6-fluoro-3-oxo-1-indanyl)acetamide (0.750 g, 0.0036 mol), N-bromosuccinimide (0.750 g, 0.0042 mol, Aldrich), benzoyl peroxide (0.270 g, 0.0011 mol, Aldrich) in tetrachloromethane (37 ml) and benzene (37 ml) was stirred while heating with an oil bath at 120° C. for 20 min. This reaction was combined with a similarly run reaction (except 0.0024 mol scale). The solution was slurried with Silica Gel 60 and the volatiles were removed by spin evaporation in vacuo. This silica gel was then applied to a column of Silica Gel 60 (51×450 mm) wet with dichloromethane and the product was removed by elution with methanol:dichloromethane (3:97). After the volatiles were removed from the combined fractions containing product by spin evaporation in vacuo, the residue was recrystallized from methanol to give 0.81 g (58%) of (E)-2-(6-fluoro-3-oxo-1-indanylidene)acetamide: m.p., 235° C. (dec.):

Workup

  1. customThis reaction was combined with a similarly run reaction (except 0.0024 mol scale)
  2. customthe volatiles were removed by spin evaporation in vacuo
  3. customthe product was removed by elution with methanol:dichloromethane (3:97)
  4. customAfter the volatiles were removed from the combined fractions
  5. additioncontaining product
  6. customby spin evaporation in vacuo
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-30a0f8b17542464fb87ee3efe2b8abee
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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