Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 1055546Notes

Reaction equation

HRID 1055546 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]CC)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 99964494-Bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene

Product 1

HCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenolYield 113%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 17a (5.0 g, 15.35 mmol, purchased from Shanghai Caerulum Pharma Discovery Co., Ltd.) in dichloromethane (50 mL) was added a solution of boron tribromide (1.7 mL, 16.89 mmol) in dichloromethane (10 mL) dropwise. The mixture was stirred at room temperature for 30 min. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate till pH becomes 7 and extracted with dichloromethane (50 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 17b as a pale yellow solid (5.16 g, 100%). This material was not further purified.

Workup

  1. extractionextracted with dichloromethane (50 mL×2)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride (30 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-446605f6d4184c14851bb2d8390f1d11
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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