1,8-Diaminonaphthalene → 2-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborine

HRID 1846037Notes

Reaction equation

HRID 1846037 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([B:8](O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]1([NH2:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[NH2:21])[CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([B:8]2[NH:22][C:11]3[C:20]4[C:15]([CH:14]=[CH:13][CH:12]=3)=[CH:16][CH:17]=[CH:18][C:19]=4[NH:21]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 680671,8-DiaminonaphthaleneHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 533844122-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborineYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-bromobenzene boronic acid (20 g, 0.1 mol) and naphthalene-1,8-diamine (17.3 g, 0.11 mol) in anhydrous toluene (600 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with petroleum ether:EtOAc 5:1 to afford the title compound as a grey solid in 54% yield, 23 g.

Workup

  1. temperatureto reflux for 16 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with petroleum ether:EtOAc 5:1

Sources & evidence

ORD record
ord-562e58f8917f4ef58c890f9fa3461faf
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…