Water → HCID 66999466, compound

HRID 558080

Reaction equation

HRID 558080 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[OH:17])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[CH:9][C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=3[O:17][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1363420412-[(4-Bromo-2-fluorophenyl)iminomethyl]-3-methylphenol

Product 1

HCID 66999466HCID 66999466, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-[(4-bromo-2-fluorophenyl)iminomethyl]-3-methylphenol (31.7 g, 102.9 mmol) in DMSO (0.27 L), K2CO3 (28.6 g, 206.9 mmol) and 18-Crown-6 (477 mg, 1.8 mmol) were added. The resulting mixture was stirred at 140° C. for 1 h and then allowed to cool to ambient temperature. Water was added and the mixture was extracted with toluene/ethyl acetate (8:2). The combined organic layers were washed with water and with brine, dried (Na2SO4) and evaporated to afford the crude compound which was purified by flash chromatography (SiO2, CH2Cl2) to give 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 84%). 1H-NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 7.01 (m, 2H), 7.18-7.37 (m, 4H), 8.77 (s, 1H). (m/z)=288+290 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was extracted with toluene/ethyl acetate (8:2)
  3. washThe combined organic layers were washed with water and with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto afford the crude compound which
  7. customwas purified by flash chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-11c3e41af9b4423fbf771a2135a8bfc0
Source dataset
uspto-grants-2011_11
Patent number
US08063037B2

Linked notes

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