Boron trifluoride etherate → Ethyl 2-(4-amino-2-fluorophenyl)acetate

HRID 1156136Notes

Reaction equation

HRID 1156136 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].B(F)(F)F.[CH3:17][CH2:18]OCC>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:17][CH3:18])=[O:11]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 187943492-(4-Amino-2-fluorophenyl)acetic acid

Product 1

HCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureto reflux for 15 hours
  2. concentrationThe solution is concentrated by distillation
  3. customevaporated to dryness in vacuo
  4. dissolutionThe residue is dissolved in ethyl ether
  5. washwashed with aqueous sodium bicarbonate
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d78aa7fd01754074bc40784b50efe0be
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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