Benzyl Alcohol → Ethyl 5-(benzyloxy)-4-fluoro-2-nitrobenzoate

HRID 1022481Notes

Reaction equation

HRID 1022481 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[C:20](F)=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([N+:22]([O-:24])=[O:23])[CH:11]=1.CCN(CC)CC>C1COCC1>[CH2:1]([O:8][C:20]1[C:10]([F:9])=[CH:11][C:12]([N+:22]([O-:24])=[O:23])=[C:13]([CH:19]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 20792112Ethyl 4,5-Difluoro-2-nitrobenzoate

Product 1

HCID 67495361Ethyl 5-(benzyloxy)-4-fluoro-2-nitrobenzoateYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.25 g of Verkade base are added to a solution of 2.61 g of benzyl alcohol in 20 ml of THF. The mixture is stirred for 10 minutes at room temperature, and a solution of 5.3 g of ethyl 4,5-difluoro-2-nitrobenzoate and 2.55 g of Et3N in 150 ml of THF is added to this solution. The mixture is stirred for 1 hour at room temperature. The reaction medium is evaporated under reduced pressure. The residue is taken up in DCM and washed three times with aqueous 1N HCl solution, and then with water. The organic phase is dried over MgSO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a PE/DCM mixture from (100/0, v/v) to (0/100, v/v) to give 4.5 g of the expected product.

Workup

  1. stirringThe mixture is stirred for 1 hour at room temperature
  2. customThe reaction medium is evaporated under reduced pressure
  3. washwashed three times with aqueous 1N HCl solution
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a PE/DCM mixture from (100/0

Sources & evidence

ORD record
ord-b329ea1cae9941eea43334a74973a797
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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