Boron tribromide → HCID 57991589, compound

HRID 556112Notes

Reaction equation

HRID 556112 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[N:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57991628HCID 57991628, compound

Product 1

HCID 57991589HCID 57991589, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 50 ml eggplant-shaped bottle were added 0.60 g (1.64 mmol) 4-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-morpholine prepared in Example 70 and 20 ml dichloromethane. The resulting mixture was cooled in ice-bath, added dropwise 2.4 ml (4.92 mmol) 2.034 mol/L solution of boron tribromide in dichloromethane, stirred in ice-bath for 1 hour and then at room temperature for 3 hours, added 2 g ice to decompose the complex. The resulting mixture was concentrated under a reduced pressure to remove dichloromethane, dissolved in 100 ml ethyl acetate, and washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, purified under a reduced pressure by silica gel column chromatography eluted with dichloromethane and methanol at a ratio 10:1-5:1 (V:V) to give a 0.26 g pale yellow thick liquid in a yield of 44.8%, 1H-NMR (DMSO-d6, 400 MHz) δ: 3.50 (2H, m, CH2), 3.63 (2H, m, CH2), 3.97 (2H, s, CH2), 4.27 (4H, s, CH2), 5.18 (1H, m), 6.97 (2H, d, J=8.40 Hz, ArH), 7.15˜7.40 (7H, m, ArH), 10.14 (1H, s, OH); EI-MS m/e (%): 352.0 (M+, 37), 322.0 (100), 240.0 (48); HREI-MS Calcd. for C20H20N2O2S: 352.1245. found: 352.1243.

Workup

  1. temperatureThe resulting mixture was cooled in ice-bath
  2. waitat room temperature for 3 hours
  3. concentrationThe resulting mixture was concentrated under a reduced pressure
  4. customto remove dichloromethane
  5. dissolutiondissolved in 100 ml ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified under a reduced pressure by silica gel column chromatography
  10. washeluted with dichloromethane and methanol at a ratio 10:1-5:1 (V:V)

Sources & evidence

ORD record
ord-e55402fbb203453a93271c929c0c0598
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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