Benzoyl Peroxide → 4-(Bromomethyl)-3-chlorobenzoic acid

HRID 7738노트

반응식

HRID 7738 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 788403-Chloro-4-methylbenzoic Acid

생성물 1

HCID 219249954-(Bromomethyl)-3-chlorobenzoic acid

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 3-chloro-4-methylbenzoic acid (5.0 g, 29 mmol), N-bromosuccinimide (5.7 g, 32 mmol), benzoyl peroxide (710 mg, 2.9 mmol) in CCl4 (300 mL) was heated at reflux for 2.5 h. The mixture was concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with 1N NaOH (3×25 mL). The aqueous mixture was acidified with 1N HCl to pH 2 and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 4-(bromomethyl)-3-chlorobenzoic acid.

후처리

  1. temperatureat reflux for 2.5 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutiondissolved in MTBE
  4. washThe organic mixture was washed with 1N NaOH (3×25 mL)
  5. extractionextracted with CH2Cl2 (3×25 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4ebe673163ca41e2bbd2f1f42373a799
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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