Hydrochloric Acid → 4-Cyclopropylbenzeneboronic acid

HRID 1038352

反応式

HRID 1038352 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[B:11](OC(C)C)([O:16]C(C)C)[O:12]C(C)C.Cl>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:11]([OH:16])[OH:12])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 122213551-Bromo-4-cyclopropylbenzene

生成物 1

HCID 28494284-Cyclopropylbenzeneboronic acid

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

2.5 M nButyllithium in hexane (14.5 mL) is added dropwise to a solution of 1-bromo-4-cyclopropyl-benzene (5.92 g) in THF (14 mL) and toluene (50 mL) chilled to −70° C. The resultant solution is stirred at −70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to −20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulphate). The solvent is evaporated and the residue is triturated with a mixture of ether and cyclohexane to give the product as a colorless solid.

後処理

  1. additionis added
  2. temperatureThe solution is warmed to −20° C.
  3. temperatureThe reaction mixture is further warmed to room temperature
  4. customthe organic phase is separated
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. dry with materialthe combined organic phases are dried (sodium sulphate)
  7. customThe solvent is evaporated
  8. customthe residue is triturated with a mixture of ether and cyclohexane

出典と根拠

ORDレコード
ord-7ac3731dc04b4cd3bf5682027ab948ca
出典データセット
uspto-grants-2013_10
特許番号
US08551957B2

関連ノート

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