Boron tribromide → HCID 178518639, compound

HRID 2392717Notes

Reaction equation

HRID 2392717 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)=[N+:5]2[O-:22].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[N+:5]2[O-:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18980361HCID 18980361, compound

Product 1

HCID 178518639HCID 178518639, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of p-methoxyphenyl nitrone 128 (2 mmol) and BBr3 (1M in CH2Cl2, 15 mL, 15 mmol) in CH2Cl2 (100 mL) was stirred for 20 h, then evaporated. The residue was evaporated with MeOH (25 mL, repeated twice), then water (50 mL) was added. The reaction mixture was basified with saturated NaHCO3 to pH 8, stirred for 1 h and acidified with 2N HCl to pH 3. The precipitated crude product was filtered, washed with water to a neutral pH, air dried and recrystallized from EtOH to give the title compound. Yield: 71%; mp 276°-278° C. (from EtOH); IR (KBr) 3422, 3069, 1670, 1653, 1609, 1590, 1459, 1361, 1297 and 1226 cm-1 ; 1H NMR (in DMSO-d6) δ6.83 (d, 2H, J=8.7 Hz), 7.41 (s, 1H), 7.99 (s, 1H), 8.27 (d, 2H, J=8.7 Hz), 10.09 (br.s, 1H, O--H), 12.53 (br.s, 1H, N--H); HPLC: 98%; HRMS Calcd for C14H8N2O3Cl2 : 321.9912.

Workup

  1. customevaporated
  2. customThe residue was evaporated with MeOH (25 mL
  3. additionwas added
  4. stirringstirred for 1 h
  5. customThe precipitated crude product
  6. filtrationwas filtered
  7. washwashed with water to a neutral pH, air
  8. customdried
  9. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-cc2b95d555a146aeb9db57fdcfd3a14a
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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