Boron trifluoride etherate → Methyl 4-(16-bromohexadecylamino)benzoate

HRID 1389651Notes

Reaction equation

HRID 1389651 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.B(F)(F)F.[CH3:32]COCC>CO>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:32])=[O:24])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 204825194-(16-Bromohexadecylamino)benzoic acid

Product 1

HCID 20482548Methyl 4-(16-bromohexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g. of 4-(16-bromohexadecylamino)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 is 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 4-(16-bromohexadecylamino)benzoate, m.p. 92°-93° C.

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-ac09a1bc5dc14ecfb284b0d94257f0bb
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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