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

HRID 2289502Notes

Reaction equation

HRID 2289502 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-3494e30677c243629a5e4e9ed44a9853
Source dataset
uspto-grants-2000_07
Patent number
US06093727

Reaction notes

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