Bromine → HCID 59854089, compound

HRID 1912112Notes

Reaction equation

HRID 1912112 reaction equation
[Cl:1][C:2]([CH3:25])([CH3:24])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([Cl:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)=[O:4].[Br:26]Br>ClC1C=CC=CC=1Cl>[Br:26][CH:11]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([Cl:22])([CH3:20])[CH3:21])=[CH:14][CH:13]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])[C:2]([Cl:1])([CH3:25])[CH3:24])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24408Bromine4×HCID 22019757HCID 22019757, compound

Product 1

HCID 59854089HCID 59854089, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Conditions

Temperature
150 °C

Procedure

A 350 ml sulfonation flask fitted with stirrer, reflux condenser and pressure equalized dropping funnel is charged with 2-chloro-1-{4-[4-(2-chloro-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one (113.1 g, 0.3 mol) and ortho-dichlorobenzene (150 ml). The mixture is heated to 150° C., and then a solution of bromine (49.6 g, 0.3 mol) in ortho-dichlorobenzene (50 ml) is added slowly in such a way that the bromine is reacted before the addition of the next drop of the bromine solution. When all the bromine has been added, the mixture is kept at 150° C. for another ten minutes, and then the ortho-dichlorobenzene is carefully removed on the rotavapor. The residue is recrystallized from hexanes to give the product (116.3 g, 85% of theory) as off white crystals, mp.=93° C. 1H-NMR (CDCl3, 400 MHz) δ 1.89 (s, 12 H, CH3); 6.29 (s, 1 H, CH); 7.54 (m, 4 H, H-4); 7.73 (m, 4 H, H-3). 13C-NMR (CDCl3, 100 MHz) δ 30.47 (C-8); 52.82 (C-1), 68.30 (C-7) 128.22 (C-3), 130.57 (C-4), 134.19 (C-5); 144.54 (C-2); 198.26 (C-6).

Workup

  1. customA 350 ml sulfonation flask fitted with stirrer
  2. temperaturereflux condenser
  3. waitthe mixture is kept at 150° C. for another ten minutes
  4. customthe ortho-dichlorobenzene is carefully removed on the rotavapor
  5. customThe residue is recrystallized from hexanes
  6. customto give the product (116.3 g, 85% of theory) as off white crystals, mp.=93° C

Sources & evidence

ORD record
ord-b01744eb5fe6476e9fa5e1811f9dd552
Source dataset
uspto-grants-2013_12
Patent number
US08604251B2

Reaction notes

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