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

HRID 508669ノート

反応式

HRID 508669 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e35bf2f15411434d96e1019b5229b4a0
出典データセット
uspto-grants-2015_08
特許番号
US09096544B2

反応ノート

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