Sodium hydride → 1-((4-Methoxybenzyloxy)methyl)-4-bromobenzene

HRID 9237

反応式

HRID 9237 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[NH4+].[Cl-]>C1COCC1.CN(C=O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 701194-Bromobenzyl alcohol

生成物 1

HCID 549706091-((4-Methoxybenzyloxy)methyl)-4-bromobenzene収率 98%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-bromobenzyl alcohol (2.011 g, 10.7 mmol) in THF (42 mL) was added to a mixture of NaH (663 mg, 16.6 mmol, 60% in oil) in DMF (13 mL). The mixture was stirred for 1.5 h and 4-methoxybenzyl chloride (MPMCl, 2 mL, 14.8 mmol) was added. After 24 h, 100 mL saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×60 mL) and the combined ethyl acetate solution was washed with water and brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 7-2 (2.43 g, 98%).

後処理

  1. waitAfter 24 h
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×60 mL)
  3. washthe combined ethyl acetate solution was washed with water and brine
  4. dry with materialThe solution was then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-505d8cde1f644863b63884fad5906a16
出典データセット
uspto-grants-2006_08
特許番号
US07091231B2

関連ノート

読み込み中…