Boron trifluoride etherate → Methyl 2-fluoro-4-hexadecylaminobenzoate

HRID 1156117Notes

Reaction equation

HRID 1156117 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].B(F)(F)F.[CH3:32]COCC>CO>[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][CH3:32])=[O:5]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 20536430Methyl 2-fluoro-4-hexadecylaminobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g of 2-fluoro-4-(hexadecylamino)benzoic acid and 34.4 ml of boron trifluoride etherate in 200 ml of methanol is stirred under reflux for 44 hours, allowed to cool, and poured into 1.20 liters of ice cold 5% aqueous sodium carbonate solution. The white solid is collected by filtration and recrystallized from benzene-ethanol to yield methyl 2-fluoro-4-(hexadecylamino)benzoate.

Workup

  1. temperatureunder reflux for 44 hours
  2. temperatureto cool
  3. filtrationThe white solid is collected by filtration
  4. customrecrystallized from benzene-ethanol

Sources & evidence

ORD record
ord-13fd65ff1e194889a3b84d04520628c0
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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