Triisopropyl borate → (2-(Benzyloxy)-4-chlorophenyl)boronic acid

HRID 269589ノート

反応式

HRID 269589 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([Li])CCC.C([O:25][B:26](OC(C)C)[O:27]C(C)C)(C)C>O1CCCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([B:26]([OH:27])[OH:25])=[C:3]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 67058419HCID 67058419、化合物HCID 178418339Butyllithium

生成物 1

HCID 69314921(2-(Benzyloxy)-4-chlorophenyl)boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

1-bromo-4-chloro-2-[(phenylmethyl)oxy]benzene (2.976 g, 10 mmol) in dry tetrahydrofuran (40 ml) was cooled to −100° C. n-Butyl lithium, 1.6M solution in hexanes (6.9 ml, 11 mmol) was added dropwise over 10 min under nitrogen. The reaction mixture was then allowed to warm to −70° C. for 1 h. Triisopropylborate (5.514, 30 mmol) was added dropwise under nitrogen. The cooling bath was then removed and the reaction mixture was allowed to warm to room temperature before being quenched with 2N hydrochloric acid (30 mL) and stirred vigorously at room temperature for 1 h. The product was then extracted with ether, dried over magnesium sulphate and evaporated down to an oil which was dissolved in iso-hexane and the solid which separated out was filtered off and dried. Yield 1.89 g.

後処理

  1. additionwas added dropwise over 10 min under nitrogen
  2. customThe cooling bath was then removed
  3. temperatureto warm to room temperature
  4. custombefore being quenched with 2N hydrochloric acid (30 mL)
  5. extractionThe product was then extracted with ether
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down to an oil which
  8. dissolutionwas dissolved in iso-hexane
  9. customthe solid which separated out
  10. filtrationwas filtered off
  11. customdried

出典と根拠

ORDレコード
ord-04cd45943b4c460b8383389dd5cdbd51
出典データセット
uspto-grants-2008_11
特許番号
US07446222B2

反応ノート

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