p-Chlorophenacyl bromide → HCID 68660928, compound

HRID 576098Notes

Reaction equation

HRID 576098 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)=[O:23]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:23])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 81531DiisopropylethylamineHCID 167857641-(3-Bromophenyl)ethanamine

Product 1

HCID 68660928HCID 68660928, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled mixture of the product from Step A (4.6 g, 23 mmol) and diisopropylethylamine (4.46 g, 34.5 mmol) in dichloromethane (50 mL) was added 2-bromo-4′-chloroacetophenone (5.48 g, 23 mmol). The reaction mixture was stirred at room temperature for 3 hours and then diluted with dichloromethane (100 mL). The mixture was washed with water and brine, dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, 20 to 40% ethyl acetate/hexanes) purification provided the 2-(1-(3-bromophenyl)ethylamino)-1-(4-chlorophenyl)ethanone (6.0 g, 74%): 1H NMR (CDCl3, 300 MHz) δ 7.80 (dd, J=6.7, 2.0 Hz, 2H), 7.52 (t, J=1.7 Hz, 1H), 7.43-7.37 (m, 3H), 7.29-7.17 (m, 2H), 3.93 (d, J=1.4 Hz, 2H), 3.80 (q, J=6.6 Hz, 1H), 1.42 (d, J=6.6 Hz, 3H). ESI MS m/z=352 [M+H]+.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customFlash chromatography (silica gel, 20 to 40% ethyl acetate/hexanes) purification

Sources & evidence

ORD record
ord-21d7e21b231d4d63aac12f46604ed2a4
Source dataset
uspto-grants-2015_05
Patent number
US09034899B2

Reaction notes

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