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Acetonitrile → 1-(Allyloxy)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene

HRID 1410293
ノート
印刷プレビュー

反応式

HRID 1410293 の反応式
[Br:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([Cl:19])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=O)[CH:7]=1.[C:22](#N)[CH3:23].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH2:21]([O:20][C:3]1[CH:4]=[C:5]([Cl:19])[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[Br:1])[CH:22]=[CH2:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71117223(5-Bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone

生成物 1

HCID 867285821-(Allyloxy)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

To a stirred −10° C. solution of (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone (54.3 mmol) from Step 4 in dichloromethane (150 mL)/acetonitrile (150 mL) was added triethylsilane (20 mL, 109 mmol) followed by boron trifluoride diethyl etherate (16 mL, 109 mmol) at −10° C. The solution was allowed to warm to 0° C. over 2 h prior to quenching with saturated sodium carbonate solution. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and water. Following extraction of the aqueous layer with ethyl acetate, the combined organic layers were washed with water prior to drying over magnesium sulfate. Filtration and concentration under reduced pressure yielded the title compound as a yellowish solid which was used without further purification.

後処理

  1. customto quenching with saturated sodium carbonate solution
  2. customAfter removal of organic volatiles under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionextraction of the aqueous layer with ethyl acetate
  5. washthe combined organic layers were washed with water
  6. dry with materialto drying over magnesium sulfate
  7. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-4b6402c0fda64e8c95ec0c46eac0204f
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921412B2

反応ノート

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