Sodium Hydroxide → 2-Bromo-4-tert-butylbenzoic acid

HRID 79091

반응식

HRID 79091 반응식
[OH-:1].[Na+].BrBr.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])C)=[C:11]([Br:18])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>O.O1CCOCC1>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:1])=[C:11]([Br:18])[CH:10]=1)([CH3:6])([CH3:7])[CH3:8]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 110971531-(4-Tert-butyl-2-bromophenyl)ethanone

생성물 1

HCID 2363522-Bromo-4-tert-butylbenzoic acid수율 100.5%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of NaOH (7.8 g, 190 mmol) in water (60 mL) was cooled in an ice bath, and bromine (2.51 mL, 49 mmol) was slowly added. A solution of 1-(4-tert-butyl-2-bromophenyl)ethanone (3.1 g, 12 mmol) in dioxane (60 mL) was slowly added, and the cooling bath was removed. After being stirred at room temperature for 3 h the reaction was acidified with concentrated hydrochloric acid. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4, and concentrated under vacuum to give 4-tert-butyl-2-bromobenzoic acid (3.1 g, 100% yield) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=8.3 Hz, 1H), 7.71 (d, J=1.9 Hz, 1H), 7.41 (dd, J=8.3, 1.9 Hz, 1H), 1.34 (s, 9H) ppm.

후처리

  1. customthe cooling bath was removed
  2. additionThe reaction was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-6b2ee0f0365b486b93bf2c85e6d4b816
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841483B2

연결된 노트

불러오는 중…