Ammonium Chloride → (4-Bromophenyl)(thiophen-2-yl)methanone

HRID 2251649ノート

反応式

HRID 2251649 の反応式
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][CH:3]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[Li].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 109992524-Bromo-N-methoxy-N-methylbenzamideHCID 178418439HCID 178418439、化合物

生成物 1

HCID 13723388(4-Bromophenyl)(thiophen-2-yl)methanone収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 4-bromobenzoyl chloride (20.0 g, 91.1 mmol) in dichloromethane (300 mL) at −78° C. was added triethylamine (28.0 mL, 200.0 mmol), and O,N-dimethylhydroxylamine hydrochloride (9.33 g, 95.6 mmol). The resulting solution was allowed to warm to room temperature, stirred for 1.5 hours, and then concentrated. The residue was triturated in acetone and the resulting solid was dissolved in ethyl acetate washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 4-bromo-N-methoxy-N-methylbenzamide (18.6 g, 84%). To a solution of 4-bromo-N-methoxy-N-methylbenzamide (3.0 g, 12.29 mmol) in THF (30 mL) at 0° C. under nitrogen was added 2-thienyllithium (1.0 M in THF, 15 mL, 15 mmol) slowly over 10 minutes. The solution was stirred at 0° C. for 1 hour, poured into a saturated aqueous ammonium chloride solution (150 mL), and extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with ether to give (4-bromophenyl)(thien-2-yl)methanone as a brown solid (1.1 g, 34%). MS (ES) m/z 266.9.

後処理

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-82328d53dd324a98b2ca1efb0d4631c9
出典データセット
uspto-grants-2008_01
特許番号
US07319152B2

反応ノート

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