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

HRID 8943

反応式

HRID 8943 の反応式
[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

参加物

6

反応物 2

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

生成物 1

HCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoate収率 60%

試薬・触媒・溶媒 3

HCID 7187Benzoyl Peroxide触媒HCID 3283Diethyl Ether溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f64e217233764463aa5656221e71fb06
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

読み込み中…