Trifluoroacetic acid → 5-Bromo-2-isopropylbenzaldehyde

HRID 72626ノート

反応式

HRID 72626 の反応式
FC(F)(F)C(O)=O.[CH:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])([CH3:10])[CH3:9].[Br:19]NC(=O)CCC(N)=O>S(=O)(=O)(O)O>[Br:19][C:16]1[CH:17]=[CH:18][C:11]([CH:8]([CH3:10])[CH3:9])=[C:12]([CH:15]=1)[CH:13]=[O:14]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 5905362-(Propan-2-yl)benzaldehydeHCID 9834204N-Bromosuccinamide

生成物 1

HCID 583408355-Bromo-2-isopropylbenzaldehyde収率 58.7%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of trifluoroacetic acid (50 ml) and 2-isopropylbenzaldehyde (2.0 g, 13.5 mmol) was added conc. sulphuric acid (98%) (10 ml) at room temperature, followed by N-bromosuccinamide (NBS, 3.6 g 20.2 mmol) in portions. After 2 hrs, the mixture was poured into ice water and extracted with dichloromethane (3×30 mL). The organic layers were combined and neutralized with saturated aqueous sodium bicarbonate, washed with brine (30 mL), dried over sodium sulfate and concentrated. The resulting residue was purified by column chromatography to furnish 5-bromo-2-isopropylbenzaldehyde (1.80 g).

後処理

  1. extractionextracted with dichloromethane (3×30 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-ee557a7feafe40a1af75b03740360b77
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

反応ノート

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