Boron tribromide → HCID 178518588, compound

HRID 2396468Notes

Reaction equation

HRID 2396468 reaction equation
[CH2:1]([C:8]1[C:9](=[O:22])[C:10]2[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=2[NH:12][C:13](=[O:17])[C:14]=1[O:15]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([C:8]1[C:9](=[O:22])[C:10]2[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=2[NH:12][C:13](=[O:17])[C:14]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19704908HCID 19704908, compound

Product 1

HCID 178518588HCID 178518588, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyl-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.45 g) in dichloromethane was added boron tribromide (4.6 mL). Upon completion of the reaction, the mixture was added to ice water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The resulting solid was recrystallized from toluene to give the title compound (0.336 g); mp 199°-200° C.; NMR: 3.97 (s,2); MS(EI): m/z=279(M). Analysis for C17H13NO3 ·0.1 H2O: Calculated: C, 72.64; H, 4.73; N, 4.98; Found: C, 72.65; H, 4.59; N, 4.94.

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. customevaporated
  6. customThe resulting solid was recrystallized from toluene

Sources & evidence

ORD record
ord-2bb205e6338c45369aa5d209326f7f56
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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