4-Chlorotoluene → [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

HRID 1865164

반응식

HRID 1865164 반응식
[Li].ClC1C=CC(C)=CC=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH:19]=[N:20][N:21]=2)=[CH:13][CH:12]=1.C([Li])CCCCC.C([O:32][B:33](OC(C)C)[O:34]C(C)C)(C)C>O1CCCC1.O.C(O)(=O)C>[O:18]1[CH:19]=[N:20][N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:11]([B:33]([OH:34])[OH:32])=[CH:12][CH:13]=1

참가 물질

9

반응물 5

HCID 78104-ChlorotolueneHCID 21531Triisopropyl borateHCID 7151202-(4-Bromophenyl)-1,3,4-oxadiazoleHCID 3028194LithiumHCID 178506865HCID 178506865, 화합물

생성물 1

HCID 10219751[4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid수율 88%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-35 °C

실험 절차

Lithium granules (8.2 g) and tetrahydrofuran (670 g) were charged to a reactor under an argon atmosphere and the mixture cooled to −35° C. 4-Chlorotoluene (74.3 g) was added at −35° C. and the mixture was held at this temperature for 6 hours. The resultant solution was added to a suspension of 2-(4-bromophenyl)-1,3,4-oxadiazole (124.4 g) in tetrahydrofuran (800 g) at −65° C. After 30 mins a solution of n-hexyllithium (33% w/w in hexanes) (240 ml) was then added at −65° C. After a further 30 min triisopropylborate (230.8 g) was then added maintaining the reaction mixture at −65° C. The reaction mixture was allowed to warm to −35° C. and drowned out into a solution of acetic acid (91.5 g) in water (688 g). The resultant solid was isolated, washed with THF and water, and dried to yield the title compound (92.2 g, 88%).

후처리

  1. temperaturemaintaining the reaction mixture at −65° C
  2. temperatureto warm to −35° C.
  3. customThe resultant solid was isolated
  4. washwashed with THF and water
  5. customdried

출처 및 근거

ORD 기록
ord-004e5e5cc6a1445dbdfe30b3a6f3729b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626020B2

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