4-Bromophenacyl bromide → HCID 57222157, compound

HRID 1646812Notes

Reaction equation

HRID 1646812 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C@@H:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[Br:27][C:28]1[CH:37]=[CH:36][C:31]([C:32](=[O:35])[CH2:33]Br)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C@@H:12]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:33][C:32]([C:31]1[CH:36]=[CH:37][C:28]([Br:27])=[CH:29][CH:30]=1)=[O:35])=[O:19]

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 18397185103187-09-3

Product 1

HCID 57222157HCID 57222157, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (7R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (0.71 g, 2.0 mmoles), p-bromophenacylbromide (0.56 g, 2.0 mmoles), and potassium carbonate (0.30 g, 2.2 mmole) in acetone (15 ml) was stirred for 2.5 hours at room temperature. After the reaction was completed, the solvent was evaporated in a reduced pressure, the residue was taken up in the isopropylether. Working up in the usual manner gave the crude product, which was chromatographed on silica gel column with isopropylether to give p-bromophenacyl (7R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoate (1.09 g, 99%) as an oil.

Workup

  1. customthe solvent was evaporated in a reduced pressure
  2. customgave the crude product, which
  3. customwas chromatographed on silica gel column with isopropylether

Sources & evidence

ORD record
ord-cae48b1503ee43cf9496d61cfd0c73a5
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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