HCID 59854089, compound → HCID 20429921, compound

HRID 2374651Notes

Reaction equation

[Cl:1][C:2]([CH3:26])([CH3:25])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[C:20]([CH3:23])([Cl:22])[CH3:21])=[CH:15][CH:14]=2)Br)=[CH:7][CH:6]=1)=[O:4].ClC(C)(C)C(C1C=CC(C(C2C=CC(C(=O)C(C)(Cl)C)=CC=2)(Br)Br)=CC=1)=[O:30]>>[Cl:1][C:2]([CH3:26])([CH3:25])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[C:20]([CH3:23])([Cl:22])[CH3:21])=[CH:15][CH:14]=2)=[O:30])=[CH:7][CH:6]=1)=[O:4]

Participants

Reactant 2

HCID 59854089HCID 59854089, compound

HCID 69037028HCID 69037028, compound

Product 1

HCID 20429921HCID 20429921, compound

Procedure

492.6 g of oil are recrystallised from 300 g of cyclohexane, followed by filtration and washing. 134 g of white crystals are obtained. From the mother liquor there are obtained, by means of concentration, a further 356 g of yellow crystals, which are recrystallised from 300 g of cyclohexane, filtered and washed with 100 g of cyclohexane. 200 g of yellowish crystals are thereby obtained. From the next mother liquor there are obtained, by means of partial concentration, a further 16.1 g of white crystals, and 112.4 g of dark-yellow oil remain. Unfortunately, all those crystal fractions of bis[4-(2-chloro-2-methyl-propionyl)-phenyl]-bromomethane are, according to the 1H NMR spectrum, mixed with the subsidiary product bis[4-(2-chloro-2-methyl-propionyl)-phenyl]-dibromomethane (the first fractions to the greatest extent). The product has been over-brominated in this experiment. The subsidiary product is expected to give rise to bis[4-(2-chloro-2-methyl-propionyl)-phenyl]-methanone during hydrolysis.

Workup

customFrom the next mother liquor there are obtained, by means of partial concentration

Sources & evidence

ORD record: ord-71d6039be83d4ffab73df69fbf278461
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462650B2

Reaction notes

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