Sodium Hydroxide → 3-Bromo-5-hydroxybenzoic acid

HRID 446272노트

반응식

HRID 446272 반응식
I[C:2]1[CH:3]=[C:4]([Br:11])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-:12].[Na+]>O>[Br:11][C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([OH:12])[CH:3]=1)[C:7]([OH:9])=[O:8]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 51825203-Bromo-5-iodobenzoic acid

생성물 1

HCID 157355113-Bromo-5-hydroxybenzoic acid

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
140 °C

실험 절차

The title compound was made according to the method described in Org. Proc. Res. Dev. 2002, 6, 591-595. To 5-iodo-3-bromo-benzoic acid (500 mg, 1.53 mmol), NaOH (250 mg, 6.1 mmol), Cu2O (240 mg, 1.68 mmol) was added water (4.0 mL). The mixture was heated for 1.5 h at 140° C. in a sealed tube. The cooled mixture was diluted with water and extracted with CH2Cl2. The aqueous layer was acidified (pH˜2) with TFA and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, concentrated and purified by reverse-phase HPLC to yield 3-bromo-5-hydroxy-benzoic acid. 1H NMR (400 MHz, DMSO-d6): 10.30 (s, 1H), 7.46 (m, 1H), 7.31 (m, 1H), 7.17 (m, 1H).

후처리

  1. extractionextracted with CH2Cl2
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse-phase HPLC

출처 및 근거

ORD 기록
ord-dd75a7ee621f4db8a2d012ed79effc1b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476434B2

반응 노트

불러오는 중…