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

HRID 9237

반응식

HRID 9237 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 549706091-((4-Methoxybenzyloxy)methyl)-4-bromobenzene수율 98%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-505d8cde1f644863b63884fad5906a16
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091231B2

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