Benzaldehyde → HCID 22144525, compound

HRID 1824791Notes

Reaction equation

HRID 1824791 reaction equation
C([SiH2]Cl)(C)(C)C.[Br:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([N+:16]([O-])=O)[C:9]=1[OH:19].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.[Cl-].[Cr+2].[Cl-].[Mn]>[Br:7][C:8]1[C:9]2[O:19][C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:16][C:10]=2[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 112651402-Bromo-4-methoxy-6-nitrophenolHCID 101645068HCID 101645068, compound

Product 1

HCID 22144525HCID 22144525, compound

Reagents, catalysts & solvents 3

HCID 23930ManganeseCatalystHCID 10197677chromium(II) dichlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl-chloro-silane (0.25 ml) was added to a mixture of 2-bromo-4-methoxy-6-nitro-phenol (0.124 g), chromium (II) chloride (0.012 g) and manganese (0) powder (0.137 g) in dimethylformamide (3 mL). The mixture was subjected to microwaves for 4 min at 150° C. Benzaldehyde (0.06 mL) was added and the reaction was subjected to microwaves for 6 min at 150° C. Water (0.5 mL) was added, then after 30 min the mixture was filtered through a pad of celite. The above procedure was repeated three more times. The combined filtrate was partitioned between dilute aq. HCl (100 mL) and ethyl acetate (100 mL). The organic layer was dried over sodium sulfate, filtered through celite and concentrated. Chromatography on silica gel (eluant: gradient 0 to 30% ethyl acetate:hexane) afforded 7-bromo-5-methoxy-2-phenyl-benzooxazole (0.13 g). MS: 304 (95%), 306.4 (100%) (MH+); HPLC tR: 2.79 min.

Workup

  1. waitthe reaction was subjected to microwaves for 6 min at 150° C
  2. filtrationafter 30 min the mixture was filtered through a pad of celite
  3. customThe combined filtrate was partitioned between dilute aq. HCl (100 mL) and ethyl acetate (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered through celite and
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e61e9eb7c38d49e893c5dae203141b77
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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