Boron tribromide → HCID 178423903, compound

HRID 726195Notes

Reaction equation

HRID 726195 reaction equation
C[O:2][C:3]1[C:4](=[O:16])[NH:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[C:4](=[O:16])[NH:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10512937HCID 10512937, compound

Product 1

HCID 178423903HCID 178423903, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 3-methoxy-9-methyl-1H-1-benzazepine-2,5-dione (39, 200 mg, 921 μmol) in dry CH2Cl2 (2 mL, distilled from CaH2) under N2, there was added a solution of BBr3 in CH2Cl2 (2 mL, 1M, Aldrich) in one portion at rt. The reaction instantaneously became homogeneous and yellow, then a yellow precipitate formed after a few seconds. The reaction was allowed to stir under N2 at rt for 45 min. The reaction was added to saturated NaHCO3 (15 mL) and the resulting beige suspension was allowed to stir for 15 min to give a cloudy, orange solution. The solution was filtered through glass wool to remove any suspended matter. The resulting solution was acidified with concd HCl (pH 2), the solid collected by filtration and washed to neutrality with water (5×2 mL). The damp filter cake was crystallized from 95% EtOH (dissolved in 15 mL, hot filtered, concd to 7 mL) to yield 43 as brown needles (98 mg, 52%, pure by TLC, 1H NMR and C,H,N analyses); mp 184°-185.5° C. (EtOH), 1H NMR (DMSO-d6) δ2.46 (s, 3H), 6.28 (s, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 8.03 (d, J=7.8 Hz, 1H), 9.94 (s, 1H), 10.85 (bs, 1H); Anal. Calcd for C11H9NO3.0.5 H2O: C, 62.26; H, 4.75; N, 6.60. Found: C, 62.39; H, 4.53; N, 6.51.

Workup

  1. customThe reaction instantaneously became homogeneous
  2. customyellow, then a yellow precipitate formed after a few seconds
  3. stirringto stir for 15 min
  4. customto give a cloudy, orange solution
  5. filtrationThe solution was filtered through glass wool
  6. customto remove any suspended matter
  7. filtrationthe solid collected by filtration
  8. washwashed
  9. customThe damp filter cake was crystallized from 95% EtOH (dissolved in 15 mL, hot filtered, concd to 7 mL)

Sources & evidence

ORD record
ord-dbb5672378104bd8b493880cf4791e31
Source dataset
uspto-grants-1998_01
Patent number
US05708168

Reaction notes

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