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

HRID 1836276Notes

Reaction equation

HRID 1836276 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, 47% 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

Sources & evidence

ORD record
ord-90aef6e56a7f4ef6bd3389cd3f488e48
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

Loading…