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

HRID 1053990Notes

Reaction equation

HRID 1053990 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 897136(2-(Benzyloxy)-5-bromophenyl)methanolYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-49784bf2b64543a3af389cf68fa4d567
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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