Hydrochloric Acid → 4-Octyloxybiphenyl-4'-yl boronic acid

HRID 915498

反応式

HRID 915498 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[B:23](OC)([O:26]C)[O:24]C.Cl>CCCCCC.C1COCC1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:23]([OH:26])[OH:24])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 28017871-Bromo-4-(4-octoxyphenyl)benzene

生成物 1

HCID 108535444-Octyloxybiphenyl-4'-yl boronic acid収率 73%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A solution of n-butylithium (50.97 cm3, 0.1274 mol, 2.5M in hexane) was added dropwise to a cooled (−78° C.) stirred solution of 4-bromo-4′-octyloxybiphenyl (40.00 g, 0.1108 mol) in THF (400 cm3). After 1 h, trimethyl borate (23.05 g, 0.2216 mol) was added dropwise to the reaction mixture maintaining a temperature of −78° C. The reaction mixture was allowed to warm to room temperature overnight. 20% hydrochloric acid (350 cm3) was added and the resultant mixture stirred for 1 h. The product was extracted into diethyl ether (3×300 cm3). The combined organic layers were washed with water (300 cm3), dried (MgSO4), filtered and the filtrate evaporated down under partially reduced pressure. The crude product was stirred with hexane for 30 minutes and filtered off to yield a white powder (26.20 g, 73%, m.pt. 134-136° C.).

後処理

  1. temperaturemaintaining a temperature of −78° C
  2. temperatureto warm to room temperature overnight
  3. extractionThe product was extracted into diethyl ether (3×300 cm3)
  4. washThe combined organic layers were washed with water (300 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe filtrate evaporated down under partially reduced pressure
  8. filtrationfiltered off

出典と根拠

ORDレコード
ord-d5238354f4f344b396e465dadcf99867
出典データセット
uspto-grants-2007_09
特許番号
US07265163B2

関連ノート

読み込み中…