Boron tribromide → HCID 28303003, compound

HRID 1986404Notes

Reaction equation

HRID 1986404 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([S:13]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([S:13]([NH:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 688754243-Methoxy-N-[2-(4-morpholinyl)ethyl]benzenesulfonamide

Product 1

HCID 28303003HCID 28303003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of boron tribromide (1M in CH2Cl2, 20 mL, 20 mmol) was added to a −78° C. solution of the product of Step 1 in CH2Cl2 (50 mL) and the resulting mixture was allowed to warm to 0° C. After 2 h at 0° C. the mixture was re-cooled to −78° C. and quenched with sat. aq. NaHCO3 solution and allowed to warm to rt. The mixture was extracted with EtOAc, and the organic layers was washed with H2O and brine, dried (MgSO4), filtered and the filtrate was concentrated to give the title compound as a crude oil (1.9 g, 66%) which was used directly in the next step. MS (ES+) m/e 287 [M+H]+.

Workup

  1. temperatureAfter 2 h at 0° C. the mixture was re-cooled to −78° C.
  2. customquenched with sat. aq. NaHCO3 solution
  3. temperatureto warm to rt
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organic layers was washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef4fbb232fd8499db0bd9af17d59eba5
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

Loading…