Benzyl Bromide → 5-(1-Adamantyl)-4-benzyloxy-2-methoxyphenyl bromide

HRID 508669노트

반응식

HRID 508669 반응식
[C:1]12([C:11]3[CH:16]=[C:15]([Br:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=3[OH:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]12([C:11]3[C:12]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:13][C:14]([O:18][CH3:19])=[C:15]([Br:17])[CH:16]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 873106562-(1-Adamantyl)-4-bromo-5-methoxyphenol

생성물 1

HCID 672090725-(1-Adamantyl)-4-benzyloxy-2-methoxyphenyl bromide수율 76.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 2-(1-adamantyl)-4-bromo-5-methoxyphenol (2.59 g, 7.68 mmol) in acetone (26 mL) was added benzyl bromide (1.31 g, 7.68 mmol) followed by K2CO3 (1.33 g, 9.60 mmol). The mixture was stirred and heated at reflux for 17.25 h under argon. Acetone was removed at reduced pressure before 1 N HCl (40 mL) was added. The mixture was extracted with EtOAc (100 mL), and the organic layer was washed with H2O and brine and dried. After removal of solvent at reduced pressure, the residue was purified on silica gel (0% to 4% EtOAc/hexane) to give 2.50 g (76%) of 5-(1-adamantyl)-4-benzyloxy-2-methoxyphenyl bromide as a white solid, mp 124-126° C. IR 2902, 2847, 1498, 1161 cm−1; 1H NMR (CDCl3) δ 1.71 (bs, 6H, AdCH2), 2.02 (bs, 311, AdCH), 2.08 (bs, 6H, AdCH2), 3.82 (s, 3H, OCH3), 5.12 (s, 2H, C6H5CH2), 6.53 (s, 1H, 3-ArH), 7.34 (s, 1H, 6-ArH), 7.31-7.50 ppm (m, 5H, C6H5).

후처리

  1. temperatureheated
  2. temperatureat reflux for 17.25 h under argon
  3. customAcetone was removed at reduced pressure before 1 N HCl (40 mL)
  4. additionwas added
  5. extractionThe mixture was extracted with EtOAc (100 mL)
  6. washthe organic layer was washed with H2O and brine
  7. customdried
  8. customAfter removal of solvent at reduced pressure
  9. customthe residue was purified on silica gel (0% to 4% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-e35bf2f15411434d96e1019b5229b4a0
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096544B2

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