Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(4-fluoronaphthalen-1-yl)-3-methylbutan-1-one

HRID 33578

反応式

HRID 33578 の反応式
[CH3:1][CH:2]([CH3:17])[CH2:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([F:16])=[CH:8][CH:7]=1)=[O:5].[Br-:18].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[Br:18][CH:3]([CH:2]([CH3:17])[CH3:1])[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([F:16])=[CH:8][CH:7]=1)=[O:5]

参加物

4

反応物 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 597968761-(4'-Fluoronaphth-1-yl)-3-methylbutan-1-one

生成物 1

HCID 597968732-Bromo-1-(4-fluoronaphthalen-1-yl)-3-methylbutan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-methyl-1-(4′-fluoronaphth-1-yl)butan-1-one (7 g) in anhydrous tetrahydrofuran (80 ml) was added phenyltrimethylammonium tribromide (11.5 g). The resulting mixture was stirred overnight at ambient temperature then partitioned between petroleum ether and water. The organic layer was separated, washed with water, brine, dried with sodium sulphate, filtered and evaporated in vacuo to yield crude 2-bromo-1-(4′-fluoronaphth-1-yl)-3-methylbutan-1-one. Sodium acetate (2.75 g) and anhydrous dimethylformamide (30 ml) were added and the resulting mixture was stirred at 80° C. for 5 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was back-extracted once with ethyl acetate. The combined organic layers were washed with water, brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (4.8 g) was obtained following silica gel column chromatography of the residue in 30-100% dichloromethane in petroleum ether.

後処理

  1. customthen partitioned between petroleum ether and water
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-da0f4d5ea2dc42be965ecf9c6fdc8f16
出典データセット
uspto-grants-2008_09
特許番号
US07429607B2

関連ノート

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