Benzyl Bromide → 1-Bromo-3-benzyloxy-4,5-difluorobenzene

HRID 602053노트

반응식

HRID 602053 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>CCOC(C)=O.O.CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([F:9])=[C:4]([F:10])[CH:3]=1

참가 물질

8

반응물 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27733075-Bromo-2,3-Difluorophenol

생성물 1

HCID 574706011-Bromo-3-benzyloxy-4,5-difluorobenzene수율 0.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of DMF (100 mL), 5-bromo-2,3-difluorophenol (10 g, 47.85 mol), and K2CO3 (7.27 g, 52.63 mol) and benzyl bromide (9 g, 52.63 mol) were combined at 0° C. under N2. The solution was allowed to warm to rt and stirred overnight. H2O, Et3N (2 eq) and EtOAc (5000 mL) were added and the organic layer separated. The aqueous layer was washed with EtOAc (2×) and the combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×), dried, and concentrated. The crude product was purified by Biotage (gradient 100% hexanes-60% EtOAc/hexanes) to afford 10.08 g of product as an oil.

후처리

  1. customwere combined at 0° C. under N2
  2. customthe organic layer separated
  3. washThe aqueous layer was washed with EtOAc (2×)
  4. washthe combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×)
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by Biotage (gradient 100% hexanes-60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-9499e05c84fc469890fe976704da6dab
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902394B2

반응 노트

불러오는 중…