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

HRID 1597343Notes

Reaction equation

HRID 1597343 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) eluding 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-8874a6112f8343cf888556969f955789
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

Loading…