Isoamyl Nitrite → HCID 19006181, compound

HRID 1885149Notes

Reaction equation

HRID 1885149 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)N.C(ON=O)CC(C)C.[Si:17]([O:24][CH2:25][C:26]1[O:27][CH:28]=[CH:29][CH:30]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C:28]2[O:27][C:26]([CH2:25][O:24][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])=[CH:30][CH:29]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 115623-BromoanilineHCID 10976930tert-Butyl[(furan-2-yl)methoxy]dimethylsilane

Product 1

HCID 19006181HCID 19006181, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of m-bromoaniline (6.88 g; 0.04M) in 42.2 g (0.2M) of 2-(t-butyldimethylsilyloxymethyl)furan at 0° was added isoamylnitrite (10.75 mL: 0.08M) dropwise over a period of 0.5 hr. The resulting mixture was then heated 16 hours at 50° C. The reaction mixture was cooled and diluted with 150 mL of ether and washed with 2×100 mL of ice cold water. The organic phase was dried over anhydrous magnesium sulfate, and the residue was distilled after filtering through 50 G of silica gel bed, to give 26% of the desired 2-(3'-bromophenyl)-5-(t-butyldimethylsilyloxymethyl)furan as a colorless liquid boiling at 163°-7°/~0.5 mm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 2×100 mL of ice cold water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. distillationthe residue was distilled
  5. filtrationafter filtering through 50 G of silica gel bed

Sources & evidence

ORD record
ord-7b60b99368ce435f8741138e397fa8e8
Source dataset
uspto-grants-1992_09
Patent number
US05143914

Reaction notes

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