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

HRID 79091

反応式

HRID 79091 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 2363522-Bromo-4-tert-butylbenzoic acid収率 100.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6b2ee0f0365b486b93bf2c85e6d4b816
出典データセット
uspto-grants-2014_09
特許番号
US08841483B2

関連ノート

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