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

HRID 1106157Notes

Reaction equation

HRID 1106157 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-0c4602f7d02141de8646ad97174b60cc
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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