1,2-Dibromobenzene → 2-Bromo-1-(3,4-dibromo-phenyl)-ethanone

HRID 352564

Reaction equation

BrC1SC(Cl)=C(Cl)C=1C(=O)CCl.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20].[Br:21][CH2:22][C:23](Br)=[O:24]>>[Br:21][CH2:22][C:23]([C:17]1[CH:18]=[CH:19][C:14]([Br:13])=[C:15]([Br:20])[CH:16]=1)=[O:24]

Participants

Reactant 3

HCID 114141,2-Dibromobenzene

HCID 61147Bromoacetyl bromide

HCID 6539169Chloromethyl Thienyl Ketone deriv. 5

Product 1

HCID 102155392-Bromo-1-(3,4-dibromo-phenyl)-ethanoneYield 13%

Procedure

General procedure described for compounds 1 and 2 starting from 1,2-dibromobenzene and bromoacetyl bromide. Purified by column chromatography column (hexane:ethyl acetate 6:1), yield 13% m.p. 60-61° C., 1H-NMR (CDCl3): δ8.2 (s, 1H, Ar), 7.8 (d, 2H, Ar), 4.4 (s, 2H, CH2); 13C-NMR (CDCl3): δ189.7 (CO), 134.6 (CH), 134.4 (CH), 134.3 (C—CO), 132.0 (C—Br), 128.8(CH), 126.2 (C—Br), 30.4 (CH2); M/z (EI): 360, 358, 356, 354 (M+, 5, 14, 14, 5%), 265, 263, 261 (M-CH2Br, 62, 100, 65%); HPLC: Column μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=8.73 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50.

Workup

customPurified by column chromatography column (hexane:ethyl acetate 6:1), yield 13% m.p. 60-61° C., 1H-NMR (CDCl3): δ8.2 (s, 1H, Ar), 7.8 (d, 2H, Ar), 4.4 (s, 2H, CH2)
customColumn μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=8.73 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50

Sources & evidence

ORD record: ord-59c35fb507c348f3979cb587c79be03a
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747057B2

Linked notes

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