Hydrochloric Acid → 3,5-Dimethylbiphenyl-4-ylboronic acid

HRID 341689ノート

反応式

HRID 341689 の反応式
C([Li])(C)(C)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:11]([CH3:13])[CH:12]=1.C[O:21][B:22](OC)[O:23]C.Cl>O1CCCC1>[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[CH3:6][C:7]1[C:12]([B:22]([OH:23])[OH:21])=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 869273,5-DimethylbiphenylHCID 178418306HCID 178418306、化合物

生成物 2

HCID 78922-MethylpentaneHCID 594504813,5-Dimethylbiphenyl-4-ylboronic acid収率 186.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

tert-Butyllithium (1.7 M solution in hexane, 36.2 ml, 61.6 mmol) is added dropwise to a solution of 3,5-dimethylbiphenyl (7.27 g, 28 mmol) in dry tetrahydrofuran (150 ml) at −78° C. under an atmosphere of nitrogen. The reaction mixture is stirred at −78° C. for 30 minutes, then trimethylborate (9.54 ml, 84 mmol) is added. The resulting mixture is stirred at −78° C. for 30 minutes and then allowed to warm to room temperature. The reaction mixture is acidified with 10% aqueous hydrochloric acid solution and extracted with diethyl ether (2×150 ml). The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give a yellow solid. Trituration with isohexane gives 3,5-dimethylbiphen-4-ylboronic acid as a white powder (5.89 g).

後処理

  1. stirringThe resulting mixture is stirred at −78° C. for 30 minutes
  2. temperatureto warm to room temperature
  3. extractionextracted with diethyl ether (2×150 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customto give a yellow solid

出典と根拠

ORDレコード
ord-9b668601273d45edbebdb6c48cea7c55
出典データセット
uspto-grants-2014_11
特許番号
US08895761B2

反応ノート

読み込み中…