Ethyl bromoacetate → HCID 65435733, compound

HRID 929175Notes

Reaction equation

HRID 929175 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].C(N(C(C)C)CC)(C)C.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(#N)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 65435733HCID 65435733, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 4-bromo-3-fluoro-aniline (120 g, 0.63 mol) and diisopropylethylamine (162 g, 1.26 mol) in acetonitrile (1.0 L) was heated to 60° C. and ethyl bromoacetate (105 g, 0.63 mol) was added dropwise within 2 h. The reaction mixture was stirred at this temperature for 12 h and was then evaporated to dryness. Water was added to the residue and the solid was filtered. Crystallization from petroleum ether and ethyl acetate (5:1) provided the desired product as a white solid.

Workup

  1. customwas then evaporated to dryness
  2. additionWater was added to the residue
  3. filtrationthe solid was filtered
  4. customCrystallization from petroleum ether and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-b9f003a4aaf04d588238f9f6d5929353
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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