Triphenylphosphine → 5-Bromo-1,3-difluoro-2-[(octan-2-yl)oxy]benzene

HRID 1712203

반응식

HRID 1712203 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][C@H:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([F:8])[C:5]=1[O:9][CH:12]([CH3:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2723888(+)-2-OctanolHCID 27362924-Bromo-2,6-difluorophenol

생성물 1

HCID 684999825-Bromo-1,3-difluoro-2-[(octan-2-yl)oxy]benzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

12.0 g of 4-bromo-2,6-difluorophenol, 10.0 ml of (S)-(+)-2-octanol and 16.5 g of triphenylphosphine were dissolved in 300 ml of tetrahydrofuran at about 20° C. with stirring under a nitrogen atmosphere. 12.5 ml of anhydrous (max. 0.0075% of H2O) diisopropyl azodicarboxylate were subsequently added dropwise. The reaction proceeds exothermically. The rate of addition was selected in such a way that the temperature of the mixture did not exceed 45° C. The reaction solution was subsequently stirred for 2 h, and the solvent was then removed in a rotary evaporator. The crude product was purified in a mixture of chlorobutane and heptane in the ratio 1:1 over 2 l of silica gel, giving 14.5 g of 3,5-difluoro-4-(1-methylheptyloxy)bromobenzene as a clear liquid.

후처리

  1. additionThe rate of addition
  2. customdid not exceed 45° C
  3. stirringThe reaction solution was subsequently stirred for 2 h
  4. customthe solvent was then removed in a rotary evaporator
  5. customThe crude product was purified in a mixture of chlorobutane and heptane in the ratio 1:1 over 2 l of silica gel

출처 및 근거

ORD 기록
ord-9693b3f43740458d867d347e8f2aae7b
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790929B2

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