홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,3-Dibromobenzene → 3-Bromobiphenyl

HRID 248136
노트
인쇄 미리보기

반응식

HRID 248136 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.B(O)O.C([Li])CCC.B(OC(C)C)(OC(C)C)OC(C)C.[OH-].[Na+].I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CCOCC.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:4]1[CH:3]=[C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:7]=[CH:6][CH:5]=1
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

12

반응물 7

HCID 79271,3-Dibromobenzene2회HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 14798Sodium HydroxideHCID 21531Triisopropyl borateHCID 61668Boronic Acid2회HCID 178418339Butyllithium

생성물 1

HCID 164493-Bromobiphenyl

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Starting with readily available starting materials, 1,3-dibromobenzene and the appropriately substituted iodobenzene, it is possible to prepare biphenyls having 3', 4' and 5' position substitution. Referring to Flow Sheet AE 1,3-dibromobenzene AE1 is converted to boronic acid AE2 by first reacting with butyl lithium in anhydrous THF or ether at about -78° C. followed by addition of triisopropyl borate. The resultant intermediate is worked up with sodium hydroxide and acidified. Boronic acid AE2 is subsequently reacted with the appropriate iodobenzene AE3 in toluene and aqueous sodium carbonate with tetrakistriphenylphosphinepalladium as a catalyst to produce the 3-bromo biphenyl B1. This reaction to B1 is well known in art with reference made herein to N. Miyaura, T. Yanagi and A. Suzuki, Syn. Comm., 11, 513 (1981). ##STR19##

출처 및 근거

ORD 기록
ord-c162315141934898b8ef634f75735e1c
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05208329

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차출처 및 근거반응 노트