N-bromobutanimide → 1-(Bromomethyl)-4-chloro-2-iodobenzene

반응식

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([I:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[I:9]

참가 물질

실험 절차

A mixture of 4-chloro-2-iodo-1-methylbenzene (3.95 g, 15.6 mmol), N-bromosuccinimide (3.10 g, 17.6 mmol), and benzoyl peroxide (0.1 g) in carbon tetrachloride (100 mL) was heated to reflux for 48 hours, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes to provide 3.34 g (64%) of the desired product. MS (DCI/NH3) m/z 330, 332 (M+H)30; 1H NMR (CDCl3) δ 7.85 (d, 1H), 7.40-7.32 (m, 2H), 4.59 (s, 2H).

후처리

temperaturewas heated
temperatureto reflux for 48 hours
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes

출처 및 근거

ORD 기록: ord-0c73544aaf074639b176ee31bd481435
출처 데이터셋: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07211595B2

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참가 물질

반응물 2

HCID 67184N-bromobutanimide

HCID 141766Benzene, 4-chloro-2-iodo-1-methyl-

생성물 1

HCID 129309611-(Bromomethyl)-4-chloro-2-iodobenzene수율 64.6%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매

HCID 5943Carbon Tetrachloride용매

실험 절차

후처리

temperaturewas heated
temperatureto reflux for 48 hours
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes

출처 및 근거

ORD 기록: ord-0c73544aaf074639b176ee31bd481435
출처 데이터셋: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07211595B2

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불러오는 중…