1-Bromopropane → 2-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1690675ノート

反応式

HRID 1690675 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[C:4]([CH3:17])[C:3]=1[OH:18].Br[CH2:20][CH2:21][CH3:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:17][C:4]1[CH:5]=[C:6]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[O:18][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

生成物 1

HCID 576184902-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (500 mg, 2.02 mmol, 1 eq.), 1-bromopropane (793 mg, 6.45 mmol, 3.2 eq.), and K2CO3 (334 mg, 2.42 mmol, 1.2 eq.) in acetone (20 mL) is heated at 65° C. for 4 days. After cooling to room temperature, the reaction is concentrated, diluted with EtOAc and sequentially washed with H2O and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give 2-(3,5-Dimethyl-4-propoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as a clear oil.

後処理

  1. concentrationthe reaction is concentrated
  2. additiondiluted with EtOAc
  3. washsequentially washed with H2O and saturated aqueous NaCl
  4. dry with materialThe organic solution is dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d6f8e605e434f208aef6342a71d9c6a
出典データセット
uspto-grants-2012_04
特許番号
US08153671B2

反応ノート

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