Boron tribromide → HCID 178439741, compound

HRID 2392551Notes

Reaction equation

HRID 2392551 reaction equation
[CH2:1]([C:4]1[C:5](=[O:19])[C:6]2[CH:17]=[CH:16][C:15]([Cl:18])=[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>[CH2:1]([C:4]1[C:5](=[O:19])[C:6]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:7]=2[NH:8][C:9](=[O:13])[C:10]=1[OH:11])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18979997HCID 18979997, compound

Product 1

HCID 178439741HCID 178439741, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-allyl-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.159 g) in dichloromethane (10 mL) was added boron tribromide (1M in dichloromethane, 1.8 mL). After 1.5 hours, the reaction mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate. Dichloromethane (30 mL) was added and the mixture was adjusted to pH 3 using 2.4N hydrochloric acid. The organic portion was separated, washed (water, brine), dried and evaporated. The resulting yellowish solid was triturated with hexanes to afford the title compound (0.074 g); mp 172°-174° C.; NMR: 11.73 (s,1), 10.39 (s,1), 7.93 (d,1, J=8.6), 7.48 (s,1), 7.30 (dd,1, J=8.8, 2.1), 5.86-5.73 (m,1), 5.01-4.91 (m,2), 3.35 (m,2). Analysis for C13H10ClNO3.0.25 H2 O: Calculated: C, 58.22; H, 3.95; N, 5.22; Found: C, 58.18; H, 3.91; N, 5.13.

Workup

  1. customthe reaction mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate
  2. additionDichloromethane (30 mL) was added
  3. customThe organic portion was separated
  4. washwashed (water, brine)
  5. customdried
  6. customevaporated
  7. customThe resulting yellowish solid was triturated with hexanes

Sources & evidence

ORD record
ord-a535c1e42d224ce1a895bfb76769a4f6
Source dataset
uspto-grants-1998_09
Patent number
US05801168

Reaction notes

Loading…