Benzyl Bromide → (2-(Benzyloxy)-5-bromophenyl)methanol

HRID 536570

反応式

HRID 536570 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[OH-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[CH2:13]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH2:7][OH:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 753425-Bromo-2-hydroxybenzyl alcohol

生成物 1

HCID 897136(2-(Benzyloxy)-5-bromophenyl)methanol収率 82.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A solution of 5-bromo-2-hydroxybenzylalcohol (3.677 g, 18.11 mmol) in abs. EtOH (80 ml) and NaOH (0.797 g, 19.921 mmol) was stirred under a N2 atmosphere for 20 min at RT then a solution of benzylbromide (2.15 ml, 18.11 mmol) in abs. EtOH (10 ml) was added and the mixture was stirred at RT overnight. The volatiles was removed under vacuum. The reminder was partitioned between HCl (2M aq.) and EtOAc. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by MPLC (50 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc) yielding 4.36 g of (2-benzyloxy-5-bromo-phenyl)-methanol.

後処理

  1. customThe volatiles was removed under vacuum
  2. customThe reminder was partitioned between HCl (2M aq.) and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by MPLC (50 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc)

出典と根拠

ORDレコード
ord-fdeb12b724ac4df7874bda2fa5aabaad
出典データセット
uspto-grants-2014_10
特許番号
US08859606B2

関連ノート

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