Boron tribromide → HCID 178524888, compound

HRID 862226Notes

Reaction equation

HRID 862226 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:17]([OH:19])=[O:18])[NH:15][CH:16]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:17]([OH:19])=[O:18])[NH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490054HCID 178490054, compound

Product 1

HCID 178524888HCID 178524888, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the ethyl ester of 13e (1.15 g, 4.0 mmol) in dry dichloromethane (50 ml) was treated with boron tribromide (16 ml, 1.0M solution in CH2 Cl2, 16.0 mmol) at 0° C. After 15 min at 0° C., the mixture was warmed to 25° C. and stirred for 16 h. The reaction mixture was cooled in an ice bath and quenched with a dropwise addition of water (20 ml). The resulting mixture was briefly stirred at 25° C. then filtered. The filtrate was carefully neutralised by the addition of solid NaHCO3 to afford 13f (700 mg, 71%) as a white solid: m.p. 186°-187 C. (decomp.) (recrystallised from MeOH); IR (KBr) 3500-2400, 2935, 1640, 1516, 1396, 1232; 1H NMR(d6 -DMSO) δ 9.83 (3H, bs), 7.16 (1H, s), 6.98 (2H, d, J=8.2), 6.66 (2H, d, J=8.2), 2.60-2.40 (4H, m), 1.84 (2H, m). Anal. Calcd for C13H14N2O3 : C, 63.40; H, 5.73; N, 11.38. Found: C, 62.96; H, 5.70; N, 11.27.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customquenched with a dropwise addition of water (20 ml)
  3. stirringThe resulting mixture was briefly stirred at 25° C.
  4. filtrationthen filtered
  5. additionThe filtrate was carefully neutralised by the addition of solid NaHCO3

Sources & evidence

ORD record
ord-b372208b4b214895b5af7f6527681abf
Source dataset
uspto-grants-1998_02
Patent number
US05716929

Reaction notes

Loading…