Bromine → 7-Amino-8-bromo-3,4-dihydronaphthalen-1(2H)-one

HRID 361391

Reaction equation

HRID 361391 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13]Br>C(O)(=O)C>[NH2:1][C:2]1[C:11]([Br:13])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 154628587-Amino-8-bromo-3,4-dihydronaphthalen-1(2H)-oneYield 102.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Amino-1-tetralone (457 mg, 2.83 mmol) was dissolved in acetic acid (8 mL) and treated with bromine (150 mL, 2.91 mmol) dropwise. After 10 min., more bromine (17 mL) was added. Then the solvent was evaporated off to give a light brown solid. It was partitioned between Na2CO3 solution and EtOAc From the organic phase was obtained a semi-solid (696 mg). It was dissolved in CHCl3 and flash chromatographed over silica gel 50 g) eluting with EtOAc/hexane (1:4) to afford a yellow solid (320 mg, 470 yield): mp 93°-96° C.

Workup

  1. customThen the solvent was evaporated off
  2. customto give a light brown solid
  3. customIt was partitioned between Na2CO3 solution and EtOAc From the organic phase

Sources & evidence

ORD record
ord-6f472eee9bd542b1a9772e6913725100
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Linked notes

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