tert-Butanol → Tert-butyl 4-(bromomethyl)benzoate

HRID 1647055

反応式

HRID 1647055 の反応式
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=1.C(O)(C)(C)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 7187Benzoyl Peroxide2 回HCID 67184N-bromobutanimide2 回HCID 116297491,1-Dimethylethyl 4-methylbenzoate

生成物 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoate収率 40%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

N-Bromosuccinimide (NBS) (35.8 g, 0.20 mol) was added in several portions to a solution of 1,1-dimethylethyl 4-methylbenzoate (prepared by the reaction of the respective acid chloride with t-butanol.) (38.0 g, 0.20 mol) and benzoyl peroxide (0.36 g, 1.5 mmol) in carbon tetrachloride (1200 mL) at vigorous reflux. Another portion of benzoyl peroxide (0.36 g, 1.5 mmol) was added just before the final addition of NBS. After the foaming subsided, the reaction mixture was cooled to room temperature, washed with water (2×60 mL) and dried over magnesium sulfate. Filtration and concentration provided an oil that was purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate to give 1,1-dimethylethyl 4-bromomethylbenzoate (21.4 g) in 40% yield.

後処理

  1. washwashed with water (2×60 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customprovided an oil that
  5. customwas purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate

出典と根拠

ORDレコード
ord-ba818f1a44eb47469763929fed7d9a57
出典データセット
uspto-grants-1993_01
特許番号
US05182263

関連ノート

読み込み中…