Hydrogen Bromide → 6-Bromo-1-tetralone

HRID 1049621Notes

Reaction equation

HRID 1049621 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.N([O-])=O.[Na+].[BrH:17]>O>[Br:17][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 101050696-Bromo-1-tetraloneYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-aminotetralone (2.0 g, 12 mmol) was dissolved in 25% HBr (4.0 mL) at 0° C. and then, a solution of NaNO2 (1.0 g, 15 mmol) in water (4.0 mL) was added slowly. Afterwards, a solution of CuBr (1.8 g, 4.0 mmol) in 48% HBr (4.0 mL) was added and the reaction was stirred at room temperature for 1.5 h. The solution was quenched by adding water and extracted with EtOAc (3×10 mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 6-bromo-3,4-dihydronaphthalen-1(2H)-one (19) (66%). NMR was according to reference 5.

Workup

  1. customThe solution was quenched
  2. additionby adding water
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-dfcb76bcc1004eb69d4d06c64cb45954
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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