Boron trifluoride etherate → 4-Benzyl-6-(5-bromo-2-isopropyl-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 72622Notes

Reaction equation

HRID 72622 reaction equation
[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15]([CH:18]([C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=3[CH:27]([CH3:29])[CH3:28])O)[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>ClCCl>[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15]([CH2:18][C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=3[CH:27]([CH3:29])[CH3:28])[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 67117055(4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-(5-bromo-2-isopropyl-phenyl)-methanol

Product 1

HCID 583407934-Benzyl-6-(5-bromo-2-isopropyl-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of (4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-(5-bromo-2-isopropyl-phenyl)-methanol (1.3 g, 2.87 mmol) in dichloromethane (25 mL) was added Et3SiH (4.8 mL, 5.70 mmol) followed by BF3.OEt2 (0.74 mL, 5.7 mmol). The reaction mixture was stirred at room temperature overnight then quenched by the addition of aq. NaHCO3. The reaction mixture was extracted with ethyl acetate (3×30 mL), and the combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Crude product obtained after evaporation of the solvent was purified by silica gel column chromatography to furnish 4-Benzyl-6-(5-bromo-2-isopropyl-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (1.0 g).

Workup

  1. customthen quenched by the addition of aq. NaHCO3
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×30 mL)
  3. washthe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. customCrude product obtained
  6. customafter evaporation of the solvent
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-267ccbf99d2843fd91bec5fb86072610
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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