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

HRID 1156100Notes

Reaction equation

HRID 1156100 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-a41c4c3559a14924a84407f9f4108e11
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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