Hydrogen Bromide → 2-Bromo-3-bromomethyl-1,4-dimethoxynaphthalene

HRID 1527701Notes

Reaction equation

HRID 1527701 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15]O.[BrH:17].[Br:18]Br>C(Cl)Cl>[Br:17][C:5]1[C:4]([CH2:15][Br:18])=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanol

Product 1

HCID 104061942-Bromo-3-bromomethyl-1,4-dimethoxynaphthaleneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Alcohol 26 (9.80 g, 45.0 mmol) was dissolved in CH2Cl2 (150.0 mL) in a flame-dried 500 mL round bottom flask. Concentrated HBr (22.0 mL) was added to displace the alcohol, the solution was stirred for 2 h at room temperature. The reaction was then diluted with CH2Cl2 (300.0 mL) and Br2 (2.40 mL, 47.7 mmol) was added dropwise dissolved in CH2Cl2 (50.0 mL) at room temperature. The reaction was stirred for 6 hours further before being washed with brine, dried over MgSO4, and filtered. The resulting solid was purified using flash column chromatography (1:19 EtOAc:hexanes) to provide 36 (9.02 g, 25.1 mmol, 56%) as a yellow powder.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction was stirred for 6 hours further
  3. washbefore being washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe resulting solid was purified

Sources & evidence

ORD record
ord-5fbf8388dd744b31ae57c6f7faca8696
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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