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

HRID 1865164

反応式

HRID 1865164 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-35 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-004e5e5cc6a1445dbdfe30b3a6f3729b
出典データセット
uspto-grants-2009_12
特許番号
US07626020B2

関連ノート

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