Dichloromethane → HCID 54399810, compound

HRID 343163Notes

Reaction equation

HRID 343163 reaction equation
C(N[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1)(C)C.C([N:18]([CH2:21][CH3:22])CC)C.[Br:23][CH2:24][C:25](Br)=[O:26].[CH2:28](Cl)Cl>>[Br:23][CH:24]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:9][CH:10]=1)[C:25]([NH:18][CH:21]([CH3:22])[CH3:28])=[O:26]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 28449673HCID 28449673, compound

Product 1

HCID 54399810HCID 54399810, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 12 g of isopropyl-(4-trifluoromethoxy-phenyl)-amine, prepared as in Part A, and 9 mL of triethylamine in 150 mL of methylene chloride stirred at 0° C. is added dropwise 11 g of bromoacetyl bromide and the resulting reaction mixture is stirred overnight at RT. The organic solution is washed successively with 1N HCl, NaHCO3 and dried with Na2SO4. The solvent is removed in vacuo and the residue is purified by silica gel flash column chromatography using hexane/EtOAc 80:20 to afford 10 g of 2-Bromo-N-isopropyl-(4-trifluoromethoxy-phenyl)-acetamide: 1H NMR (300 MHz, CDCl3) δ7.31(m, 4H), 5.00 (m, 1H), 3.54 (s, 2H), 1.10 (d, 6H, J=6.8).

Workup

  1. customthe resulting reaction mixture
  2. stirringis stirred overnight at RT
  3. washThe organic solution is washed successively with 1N HCl, NaHCO3
  4. dry with materialdried with Na2SO4
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-59ea1d37595c401aae8a6eaf432b2553
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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