Sodium hydride → 3-Bromo-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether

HRID 638635

反応式

HRID 638635 の反応式
[H-].[Na+].[CH3:3][C:4]([CH3:16])([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)[CH2:5][OH:6].[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:21]Br>CN(C)C=O>[CH3:3][C:4]([CH3:16])([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH3:15])=[CH:11][CH:12]=1)[CH2:5][O:6][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([F:26])=[C:18]([Br:17])[CH:19]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1585252-(4-Ethoxyphenyl)-2-methylpropanolHCID 129227103-Bromo-4-fluorobenzyl Bromide

生成物 1

HCID 134881903-Bromo-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether収率 41.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

657 Milligrams of sodium hydride (as 60% oil suspension) was added to 10 ml of dimethylformamide, and 3.19 g of 2,2-dimethyl-2-(4-ethoxyphenyl)ethanol was added dropwise. Thereafter, the reaction solution was warmed to 50° C. and stirred for 10 minutes, and 4.0 g of 3-bromo-4-fluorobenzyl bromide was added dropwise thereto at 20° C. After completion of the dropwise addition, stirring was continued at 50° C. for further 5 hours, and the reaction solution was then poured into a 5% hydrochloric acid/ice water mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium chloride liquor and dried over anhydrous magnesium sulfate. After removing the solvent by evaporation, the residual oil was purified by column chromatography on a column packed with 60 g of silica gel to obtain 2.37 g of 3-bromo-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether. 1H-NMR spectrum (CDCl3, TMS). δ 7.4-6.5 (7H, m), δ 4.30 (2H, s), δ 3.99 (2H, q), δ 3.34 (2H, s), δ 1.36 (3H, t), δ 1.30 (6H, s).

後処理

  1. additionwas added dropwise
  2. customat 20° C
  3. additionAfter completion of the dropwise addition
  4. stirringstirring
  5. waitwas continued at 50° C. for further 5 hours
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with an aqueous sodium chloride liquor
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removing the solvent
  10. customby evaporation
  11. customthe residual oil was purified by column chromatography on a column

出典と根拠

ORDレコード
ord-df932647de5b4769ac1dd2e1faf8da60
出典データセット
uspto-grants-1985_12
特許番号
US04562213

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