Boron tribromide → HCID 178439740, compound

HRID 2392553Notes

Reaction equation

HRID 2392553 reaction equation
[CH2:1]([C:4]1[C:5](=[O:18])[C:6]2[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=2[NH:8][C:9](=[O:13])[C:10]=1[O:11]C)[CH:2]=[CH2:3].B(Br)(Br)Br>ClCCl.O>[CH2:1]([C:4]1[C:5](=[O:18])[C:6]2[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=2[NH:8][C:9](=[O:13])[C:10]=1[OH:11])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 18980008HCID 18980008, compound

Product 1

HCID 178439740HCID 178439740, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-allyl-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.2 g) in dichloromethane was added boron tribromide (1M in dichloromethane, 3 mL). The precipitate that formed was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated using toluene to azeotrope the water. The solid was recrystallized from hot toluene to give the title compound (0.14 g); mp 174°-175° C.; NMR: 5.80 (m,1); 5.03 (s,1); 4.98 (d,1); 3.38 (d,2); MS: m/z=229(M+1). Analysis for C13 H11NO3.0.1 H2O: Calculated: C, 67.58; H, 4.89; N, 6.06; Found: C, 67.63; H, 4.88; N, 5.95.

Workup

  1. customThe precipitate that formed
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. customevaporated
  6. customThe solid was recrystallized from hot toluene

Sources & evidence

ORD record
ord-56afb6fac6fa42debd1b27e46ddf7532
Source dataset
uspto-grants-1998_09
Patent number
US05801168

Reaction notes

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