Hydrogen Peroxide → 3-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

HRID 237533노트

반응식

HRID 237533 반응식
[CH2:1]([C:4]1[CH:5]=[C:6]([CH3:12])[C:7]([Br:11])=[C:8]([CH3:10])[CH:9]=1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:22].[Na+].OO>O1CCCC1>[Br:11][C:7]1[C:6]([CH3:12])=[CH:5][C:4]([CH2:1][CH2:2][CH2:3][OH:22])=[CH:9][C:8]=1[CH3:10]

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2회HCID 866971955-Allyl-2-bromo-1,3-dimethylbenzene

생성물 1

HCID 866971963-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-allyl-2-bromo-1,3-dimethylbenzene (1.0 g) is cooled to 0° C., 9-borabicyclo[3.3.1]nonane (9-BBN, 26 mL of a 0.5 M solution in tetrahydrofurane) is added dropwise and the mixture is stirred for 2 hours at room temperature. After cooling to 0° C. NaOH (6.7 mL, 4 M) and H2O2 (6.7 mL, 35%) are added dropwise. The mixture is stirred for 12 hours while warming to room temperature. Then the mixture is partitioned between brine and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30) to give the title compound. Yield: 750 mg; LC (method 8): tR=0.28 min; Mass spectrum (ESI+): m/z=260 [M+NH4]+.

후처리

  1. temperatureAfter cooling to 0° C
  2. stirringThe mixture is stirred for 12 hours
  3. temperaturewhile warming to room temperature
  4. customThen the mixture is partitioned between brine and diethylether
  5. dry with materialThe organic phase is dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30)

출처 및 근거

ORD 기록
ord-78779cab0b114c9985316c41dfa1d816
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

반응 노트

불러오는 중…