Boron trifluoride etherate → 2-Ethoxyethyl 2-fluoro-4-(hexadecylamino)benzoate

HRID 1156116Notes

Reaction equation

HRID 1156116 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:28]([O:30][CH2:31][CH2:32]O)[CH3:29].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:29][CH2:28][O:30][CH2:31][CH3:32])=[O:5]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 8076Glycol monoethyl etherHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 205364602-Ethoxyethyl 2-fluoro-4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g of 2-fluoro-4-(hexadecylamino)benzoic acid, 1.00 g. of 2-ethoxyethanol and 5.35 ml of boron trifluoride etherate in 200 ml of toluene is stirred under reflux for 48 hours. The solution is treated with an additional 5.35 ml of boron trifluoride etherate and refluxing is continued for 120 hours. Dilution with water and methylene chloride followed by filtration affords 2-ethoxyethyl 2-fluoro-4-(hexadecylamino)benzoate as a white solid.

Workup

  1. temperatureunder reflux for 48 hours
  2. temperaturerefluxing
  3. filtrationDilution with water and methylene chloride followed by filtration

Sources & evidence

ORD record
ord-3536210135b84319808c6acfcbf32908
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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