Dimethyl Sulfoxide → 2-Bromo-9,9-di-n-octylfluorene

HRID 917239

反応式

HRID 917239 の反応式
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CS(C)=O.[OH-].[Na+].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCCCCC.O.CCOCC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH3:10])([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:4]=2[CH:3]=1

参加物

8

反応物 4

HCID 679Dimethyl SulfoxideHCID 81401-BromooctaneHCID 143362-Bromo-9H-fluoreneHCID 14798Sodium Hydroxide

生成物 1

HCID 129646932-Bromo-9,9-di-n-octylfluorene収率 155.4%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 8058Hexane溶媒HCID 21584184Diethylether water溶媒

実験手順

A 3 L flask fitted with a mechanical stirrer was charged with 2-bromofluorene (45 g, 183.6 mmole) and 150 mL DMSO. Under a N2 atmosphere was added 80 mL of a 50% aqueous NaOH solution and 2.72 g of benzyltriethylammonium chloride (2.72 g, 11.98 mmole). This was stirred for 2 h at RT. With vigorous mechanical stirring, n-octylbromide (84.96 g, 440 mmole) was added via a dropping funnel (exotherm). Stirring was continued for 2 hours. To the reaction mixture was added 500 mL of a 1:1 mixture of water/ether, and the organic layer separated and was washed successively with brine and then water. Drying over magnesium sulfate and evaporation of the solvent gave an oil. Purification by column chromatography (silica gel; hexane as the mobile phase) gave 67 g (78% yield) of 2-bromo-9,9-dioctylfluorene as a pale oil.

後処理

  1. customA 3 L flask fitted with a mechanical stirrer
  2. stirringStirring
  3. waitwas continued for 2 hours
  4. additionTo the reaction mixture was added
  5. customthe organic layer separated
  6. washwas washed successively with brine
  7. dry with materialDrying over magnesium sulfate and evaporation of the solvent
  8. customgave an oil
  9. customPurification by column chromatography (silica gel

出典と根拠

ORDレコード
ord-2c83e6d3ede0462f8faadbb22600d502
出典データセット
uspto-grants-2007_09
特許番号
US07271406B2

関連ノート

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