Isoamyl Nitrite → HCID 19006181, compound

HRID 1743013Notes

Reaction equation

HRID 1743013 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 50G 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 50G of silica gel bed

Sources & evidence

ORD record
ord-4b7b6d67907b48fd956d94a746ce90f1
Source dataset
uspto-grants-1994_08
Patent number
US05342933

Reaction notes

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