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

HRID 915498

반응식

HRID 915498 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 108535444-Octyloxybiphenyl-4'-yl boronic acid수율 73%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-d5238354f4f344b396e465dadcf99867
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265163B2

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