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

HRID 7738ノート

反応式

HRID 7738 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 219249954-(Bromomethyl)-3-chlorobenzoic acid

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ebe673163ca41e2bbd2f1f42373a799
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

反応ノート

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