Triethylamine → Methyl 5-(2,2-difluoroethoxy)-2-nitrobenzoate

HRID 403557

Reaction equation

HRID 403557 reaction equation
[F:1][CH:2]([F:5])[CH2:3][OH:4].F[C:7]1[CH:8]=[CH:9][C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].CCN(CC)CC.C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C>C1COCC1>[F:1][CH:2]([F:5])[CH2:3][O:4][C:7]1[CH:8]=[CH:9][C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1361872,2-Difluoroethan-1-olHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 51520495-Fluoro-2-nitrobenzoic acid methyl ester

Product 1

HCID 59587324Methyl 5-(2,2-difluoroethoxy)-2-nitrobenzoateYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.53 g of 2,2-difluoroethanol are added to a solution of 17.31 g of methyl 5-fluoro-2-nitrobenzoate, 9.64 g of NEt3 and 32.71 g of 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane in 250 ml of anhydrous THF. The mixture is stirred at AT for 30 min. The solvent is evaporated under reduced pressure. Water is added and extraction is carried out with AcOEt. The extract is washed with a 1N aqueous HCl solution, with water and then with a saturated NaCl solution. It is dried over MgSO4 and filtered, and the solvent is evaporated under reduced pressure to give 21 g of the expected product.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. additionWater is added
  3. extractionextraction
  4. washThe extract is washed with a 1N aqueous HCl solution, with water
  5. dry with materialIt is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2113f649297a473aaf857ee42f72bf8c
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Linked notes

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