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

HRID 269589노트

반응식

HRID 269589 반응식
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

참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 67058419HCID 67058419, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-04cd45943b4c460b8383389dd5cdbd51
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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