1-Bromohexadecane → Ethyl 3-fluoro-4-(hexadecylamino)benzoate

HRID 1389076Notes

Reaction equation

HRID 1389076 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[F:13].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O.O>[F:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[NH:1][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 20536493Ethyl 4-amino-3-fluorobenzoate

Product 1

HCID 20536470Ethyl 3-fluoro-4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4.0 g of ethyl 4-amino-3-fluorobenzoate, 6.66 g of hexadecyl bromide and 3.0 g of potassium carbonate in 25 ml of hexamethyl phosphoramide is stirred at 150° C. for 20 hr. The mixture is cooled, diluted with water and extracted with ether. The ether extract is washed with water, dried, and the ether evaporated. The residue is recrystallized from hexane to yield ethyl 3-fluoro-4-(hexadecylamino)benzoate as a white solid.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. customdried
  6. customthe ether evaporated
  7. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-1bf5a9a01b0a4690ad5cf17e375f6479
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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