Acetyl chloride → HCID 16006725, compound

HRID 2355837Notes

Reaction equation

HRID 2355837 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=CC=[C:19](OC)[CH:18]=2)[CH2:9][N:10]2[C:14](=O)[CH2:13][CH2:12][C:11]2=O)=[CH:4][CH:3]=1.[C:25](Cl)(=O)[CH3:26].[CH3:29][CH2:30][O:31][C:32]([CH3:34])=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C:17]3[C:18](=[CH:19][CH:34]=[C:32]([O:31][CH2:30][CH2:29][CH2:11][N:10]4[CH2:26][CH2:25][CH2:5][CH2:8][CH2:9]4)[CH:22]=3)[C@H:14]3[CH2:13][CH2:12][CH2:11][N:10]3[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 675419221-[2-(4-Bromophenyl)-2-(3-methoxyphenyl)ethyl]pyrrolidine-2,5-dione

Product 1

HCID 16006725HCID 16006725, compoundYield 75%

Procedure

1-[2-(4-Bromo-phenyl)-2-(3-methoxy-phenyl)-ethyl]-pyrrolidine-2,5-dione. A solution of the crude product from Step 7 (54.9 mmol) in EtOAc (55 mL) was treated with acetyl chloride (14.0 mL) and then was heated at reflux overnight. The mixture was cooled, and a precipitate formed. The solid was filtered to provide 15.9 g (75%) of the desired product. The filtrate was purified by chromatography (EtOAc/hexanes) to give an additional 3.28 g, for a combined yield of 19.2 g (90%). MS: exact mass calcd for C19H18BrNO3, 387.1; m/z found, 410.0 [M+Na]+, 412.0 [M+Na]+. 1H NMR (CDCl3): 7.38 (m, 2H), 7.19 (m, 3H), 6.81 (d, J=7.6, 1H), 6.73 (m, 2H), 4.60 (t, J=8.4, 1H), 4.06 (m, 2H), 3.74 (s, 3H), 2.51 (s, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. customa precipitate formed
  5. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-13dfcc19917341c78fad293e22caff52
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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