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

HRID 1095072ノート

反応式

HRID 1095072 の反応式
[Br: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>[Br: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 37184441-Bromo-2-fluoro-4-methoxybenzeneHCID 45051747Lithium diisopropylamine

生成物 1

HCID 577432213-Bromo-2-fluoro-6-methoxybenzaldehyde収率 89%

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-bromo-3-fluoroanisole (10 g, 48.7 mmol, Matrix) in tetrahydrofuran (100 mL) at −78° C. was added lithium diisopropyl amine (32.5 mL, 1.8 M in THF, 58.4 mmol) dropwise during a period of 15 min. The mixture was stirred at −78° C. for another 20 mins. Then N,N-dimethyl-formamide (4.53 mL, 58.4 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (12 g, 194 mmol) and followed by the addition of water (61 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give 3-bromo-2-fluoro-6-methoxy-benzaldehyde as a yellow solid (Yield: 10 g, 89%)

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
  5. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

出典と根拠

ORDレコード
ord-f6d740b1e3b34751afb97d2e9fdbdb75
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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