1-Bromohexadecane → Ethyl 2-fluoro-4-(hexadecylamino)phenylacetate

HRID 1156137Notes

Reaction equation

HRID 1156137 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].Br[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][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:31][CH2:30][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][CH3:16])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetate

Product 1

HCID 54400635Ethyl 2-fluoro-4-(hexadecylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.2 g. of 2-fluoro-4-aminophenylacetic acid, 150 ml. of absolute ethanol, and 3 ml. of boron trifluoride etherate is heated to reflux for 15 hours. The solution is concentrated by distillation and then evaporated to dryness in vacuo. The residue is dissolved in ethyl ether, washed with aqueous sodium bicarbonate dried and evaporated to yield ethyl 2-fluoro-4-aminophenylacetate. A mixture of 5.0 g. of this amine, 9.4 g. of 1-bromohexadecane, 4.2 g. of anhydrous potassium carbonate and 40 ml. of hexamethylphosphoramide is heated at 80° C. for 7 hours. The mixture is then cooled, diluted with water, and extracted with ethyl ether. The ether extracts are washed with water, dried and evaporated. The residue is recrystallized from a mixture of chloroform and hexane, yielding ethyl 2-fluoro-4-(hexadecylamino)phenylacetate.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ethyl ether
  4. washThe ether extracts are washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-60af6d9b24e94573894a371e7b90a29a
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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