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

HRID 1457498

反応式

HRID 1457498 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 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

13.7 g (47.1 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 80 ml of dry THF were cooled to -75° C., and 34.0 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 12.9 g (68.7 mmol) of triisopropoxyboron and 50 ml of dry THF was dripped, and stirring at -75° C. was performed for 2 hours and that at room temperature was performed for 14 hours. After the reactions had been completed, 50 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 8.62 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained (yield 71%).

後処理

  1. stirringstirring at -75° C.
  2. waitwas performed for 2 hours and that at room temperature
  3. waitwas performed for 14 hours
  4. extractionextraction with ethyl acetate
  5. customAfter the extracted solution was dried
  6. customthe solvent was removed by filtration
  7. customwas obtained (yield 71%)

出典と根拠

ORDレコード
ord-78d4712c72084bc4b4fdf152e90d9420
出典データセット
uspto-grants-1998_12
特許番号
US05849217

関連ノート

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