N-bromobutanimide → Ethyl 2-bromomethyl-6-methoxybenzoate

HRID 8943

반응식

HRID 8943 반응식
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

생성물 1

HCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoate수율 60%

시약·촉매·용매 3

HCID 7187Benzoyl Peroxide촉매HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of ethyl 2-methoxy-6-methylbenzoate (0.813 g, 4.19 mmol) in CCl4 (8 mL) was added recrystallized N-bromosuccinimide (0.751 g, 4.22 mmol) followed by benzoyl peroxide (52 mg, 0.22 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (8:1 hexanes-EtOAc) provided 0.68 g (60%) of ethyl 6-(bromomethyl)-2-methoxybenzoate as a colorless oil. 1H NMR (CDCl3) δ 1.42 (t, 3H, J=7.2 Hz), 3.84 (s, 3H), 4.45 (q, 2H, J=7.2 Hz), 4.50 (s, 2H), 6.89 (d, 1H, J=8.4 Hz), 7.01 (d, 1H, J=7.2 Hz), 7.34 (dd, 1H, J=7.2, 8.4 Hz).

후처리

  1. temperatureto reflux for 90 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (8:1 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-f64e217233764463aa5656221e71fb06
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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