Triphenylphosphine → HCID 117620688, compound

HRID 626319Notes

Reaction equation

HRID 626319 reaction equation
N(C(OCCOC)=O)=NC(OCCOC)=O.[CH3:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([CH3:27])=[CH:20][C:19]=1[OH:28].[Br:29][C:30]1([Br:35])[CH2:32][CH:31]1[CH2:33]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:29][C:30]1([Br:35])[CH2:32][CH:31]1[CH2:33][O:28][C:19]1[CH:20]=[C:21]([CH3:27])[C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=1[CH3:17]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 2821102,5-Dimethyl-4-nitrophenolHCID 516892Sodium BicarbonateHCID 108897082,2-DibromocyclopropanemethanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 1

HCID 117620688HCID 117620688, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.85 g of Bis(2-methoxyethyl) azodicarboxylate was added to a mixture of 0.47 g of 2,5-dimethyl-4-nitrophenol, 0.64 g of (2,2-dibromocyclopropyl)methanol (manufactured according to a reference document (R. Huwyler, A. Al-Dulayymi, M. Neuenschwander, Helv. Chim. Acta 1999, 82, 2336)), 0.87 g of triphenylphosphine and 30 mL of toluene at 0° C., and the mixture was stirred at 80° C. for 5 hours. After cooling, a saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate, and then the organic layer was washed with water and saturated salt water and dried over anhydrous magnesium sulfate. The resulting residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-[(2,2-dibromo-cyclopropyl)methoxy]-2,5-dimethyl-4-nitrobenzene.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated salt water
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-9ffa8bbfa9a24193ab73d42a9ed154b9
Source dataset
uspto-grants-2016_04
Patent number
US09309191B2

Reaction notes

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