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

HRID 237533ノート

反応式

HRID 237533 の反応式
[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]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2 回HCID 866971955-Allyl-2-bromo-1,3-dimethylbenzene

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-78779cab0b114c9985316c41dfa1d816
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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