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

HRID 1647055

반응식

HRID 1647055 반응식
[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

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 7187Benzoyl Peroxide2회HCID 67184N-bromobutanimide2회HCID 116297491,1-Dimethylethyl 4-methylbenzoate

생성물 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoate수율 40%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba818f1a44eb47469763929fed7d9a57
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182263

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