Hydrochloric Acid → 5-Bromo-2-chloro-1,3-dimethoxybenzene

HRID 49281ノート

反応式

HRID 49281 の反応式
N([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[C:9](N)=[C:8]([O:15][CH3:16])[CH:7]=1.[ClH:17]>O>[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[C:9]([Cl:17])=[C:8]([O:15][CH3:16])[CH:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 3294234-Bromo-2,6-dimethoxyanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 225579025-Bromo-2-chloro-1,3-dimethoxybenzene収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524-527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-f08cb50cadf44c35b45d9834983c202c
出典データセット
uspto-grants-2004_03
特許番号
US06706703B2

反応ノート

読み込み中…