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

HRID 33578

반응식

HRID 33578 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da0f4d5ea2dc42be965ecf9c6fdc8f16
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429607B2

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