Bromochloromethane → 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone

HRID 875254ノート

反応式

HRID 875254 の反応式
Br[CH2:2][Cl:3].C[O:5][C:6]([CH:8]1[CH:13]=[CH:12][C:11]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:10]=2[O:9]1)=O.[Li]CCCC.CCCCCC>C1COCC1.O.C(O)(=O)C>[Cl:3][CH2:2][C:6]([CH:8]1[CH:13]=[CH:12][C:11]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:10]=2[O:9]1)=[O:5]

参加物

8

反応物 4

HCID 6333BromochloromethaneHCID 8058HexaneHCID 673938016-Fluoro-1-benzopyran-2-carboxylic acid methyl esterHCID 178418339Butyllithium

生成物 1

HCID 866579942-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone収率 98.6%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1.2 g of bromochloromethane (9.2 mmol) were added at room temperature to a solution of 1.0 g of crude 6-Fluoro-1-benzopyran-2-carboxylic acid methyl ester (4.7 mmol) in 15 ml of THF. The solution was then cooled to −80/−85° C. and 4.6 ml of 2.5 M n-BuLi in hexane (9.2 mmol) were slowly added to maintain the internal temperature between −75° C. and −80° C. The reaction progress was monitored by TLC. The solution was then acidified by the addition of 1 ml glacial acetic acid in 2 ml THF between −70° C. and −80° C. 5 ml of water were then added at 0° C. and the aqueous layer was then removed after decantation. The organic layer was concentrated under reduced pressure to give the title compound (1.05 g) as a yellow oil (titration by NMR: ≈80% w/w).

後処理

  1. additionwere slowly added
  2. temperatureto maintain the internal temperature between −75° C. and −80° C
  3. customthe aqueous layer was then removed after decantation
  4. concentrationThe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-5caf54fd6d514e33a96fbcf7cfa558df
出典データセット
uspto-grants-2015_03
特許番号
US08981127B2

反応ノート

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