Hydrogen Bromide → 6-Bromo-1-tetralone

HRID 594762Notes

Reaction equation

HRID 594762 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.[BrH:17]>O>[Br:17][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]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 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NaNO2 (2.35 g, 34 mmol) in water (10 mL) was added dropwise to the solution of 6-amino-1,2,3,4-tetrahydronaphthalen-1-one (5.0 g, 31 mmol) in 25% HBr (16 mL) at 0° C. The suspension was then transferred to a stirred mixture of CuBr (8.9 g, 62 mmol) in 48% HBr (30 mL) at 0° C. The resulting mixture was allowed to warm to rt and stirred for 1 h. The mixture was extracted with EtOAc, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (0%-60% EtOAc/Hex) to give 5.6 g (80%) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 2.10-2.16 (2H, m), 2.64 (2H, t, J=6.4 Hz), 2.94 (2H, t, J=6.0 Hz), 7.42 (1H, s), 7.44 (1H, s), 7.87 (1H, d, J=8.9 Hz). [M+H] calc'd for C10H9BrO, 225, 227. found 225, 227.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (0%-60% EtOAc/Hex)

Sources & evidence

ORD record
ord-feeb75d72dc448f2b9912f3b07936bb9
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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