Acetic Acid → 3-Chloro-2-fluoro-6-methoxybenzaldehyde

HRID 1095076ノート

反応式

HRID 1095076 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10].C(NC(C)C)(C)C.[Li].CN(C)[CH:21]=[O:22].C(O)(=O)C>O1CCCC1.O>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[CH:21]=[O:22]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 27245211-Chloro-2-fluoro-4-methoxybenzeneHCID 45051747Lithium diisopropylamine

生成物 1

HCID 221397073-Chloro-2-fluoro-6-methoxybenzaldehyde収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 4-chloro-3-fluoroanisole (10.2 g, 63.5 mmol, Oakwood) in tetrahydrofuran (100 mL) at −78° C. was added lithium diisopropyl amine (42.3 mL, 1.8 M in THF, 76.2 mmol) dropwise during a period of 15 min. The mixture was stirred at −78° C. for another 20 mins. Then N,N-dimethyl-formamide (5.9 mL, 76.2 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (15.6 g, 254 mmol) and followed by the addition of water (80 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated to give 3-chloro-2-fluoro-6-methoxy-benzaldehyde as a yellow solid (Yield: 10 g, 85%)

後処理

  1. stirringThe mixture was stirred at −78° C. for 10 min
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-48e648302af648bd8c1c2e8bed33d01d
出典データセット
uspto-grants-2012_03
特許番号
US08134001B2

反応ノート

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