Hydrochloric Acid → Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-

HRID 1457496

反応式

HRID 1457496 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C.Cl>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([B:27]([OH:28])[OH:26])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 219093031-(2-(Benzyloxy)ethyl)-4-bromobenzeneHCID 178418339Butyllithium

生成物 1

HCID 11543402Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3.8 g (13.0 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 30 ml of dry THF were cooled to -80° C., and 9.4 ml of n-butyllithium (1.65M) was dripped to it. Stirring at the foregoing temperature was performed for 3 hours, and then mixture solution of 5.68 g (30.2 mmol) of triisopropoxyboron and 15 ml of dry THF was dripped, and stirring at room temperature was performed for 13 hours. After the reactions had been completed, 15 ml of 10% hydrochloric acid was added, and extraction with ethyl acetate was performed. After the extracted solution was dried, the solvent was removed by filtration. Then, refining was performed with a silica gel column chromatography (developing solvent: toluene/ethyl acetate=20/1) so that 3.21 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained (yield 64%).

後処理

  1. stirringstirring at room temperature
  2. waitwas performed for 13 hours
  3. extractionextraction with ethyl acetate
  4. customAfter the extracted solution was dried
  5. customthe solvent was removed by filtration
  6. customwas obtained (yield 64%)

出典と根拠

ORDレコード
ord-b723b5d6be384cbaab574ef2a6a21752
出典データセット
uspto-grants-1998_12
特許番号
US05849217

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