1-Bromohexadecane → Methyl 2-fluoro-4-hexadecylaminobenzoate

HRID 1156097Notes

Reaction equation

HRID 1156097 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[CH2:13](Br)[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][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([NH:1][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][CH2:14][CH3:13])=[CH:3][C:4]=1[F:12]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 21957875Methyl 4-amino-2-fluorobenzoate

Product 1

HCID 20536430Methyl 2-fluoro-4-hexadecylaminobenzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 8.3 g. of methyl 4-amino-2-fluorobenzoate, 15.0 g of hexadecylbromide, 6.8 g of anhydrous potassium carbonate and 50 ml of hexamethylphosphoramide is heated to 135° for 20 hours. Upon cooling, dilution with water and extraction with ether, the orange colored ethereal extract is washed with water, dried and evaporated to yield an off-white solid. Recrystallization of this material from hexane affords methyl-2-fluoro-4-(hexadecylamino)benzoate.

Workup

  1. additionA mixture of 8.3 g
  2. temperatureUpon cooling
  3. extractiondilution with water and extraction with ether
  4. extractionthe orange colored ethereal extract
  5. washis washed with water
  6. customdried
  7. customevaporated
  8. customto yield an off-white solid
  9. customRecrystallization of this material from hexane

Sources & evidence

ORD record
ord-83f3bfdbcae149cfa340dd4ef2abe268
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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