Hydrochloric Acid → 1-(2-Bromo-5-chlorophenyl)ethanone

HRID 2415552

反応式

HRID 2415552 の反応式
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](N(OC)C)=[O:8].Cl.O>O1CCCC1.C1(C)C=CC=CC=1.O1CCCC1>[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](=[O:8])[CH3:1]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 222365462-Bromo-5-chloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 124866171-(2-Bromo-5-chlorophenyl)ethanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22635083Tetrahydrofuran toluene溶媒

実験手順

Methylmagnesium bromide (4.26 mL of a 1.4M solution in tetrahydrofuran/toluene, 5.97 mmol) was added dropwise to a stirred solution of 2-bromo-5-chloro-N-methoxy-N-methylbenzamide (3-1) (0.554 g, 1.99 mmol) in tetrahydrofuran (20 mL) at approximately 0° C. After 1 h, 1N hydrochloric acid (5 mL) was added and the resulting biphasic mixture was stirred vigorously for about 10 min. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0-10% ethyl acetate/hexanes as eluent) provided 3-3 (0.44 g) as a colorless oil.

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0-10% ethyl acetate/hexanes as eluent)

出典と根拠

ORDレコード
ord-994732bb6d2942fbb576ed31e579f72d
出典データセット
uspto-grants-2004_11
特許番号
US06818658B2

関連ノート

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