Diethyl Ether → 6-Bromonaphthalene-2-carbaldehyde

HRID 1430719Notes

Reaction equation

HRID 1430719 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH2:23][OH:24])[CH:17]=[CH:16]2.C(OCC)C>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=[O:24])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13473070(6-Bromonaphthalen-2-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 134770296-Bromonaphthalene-2-carbaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of pyridinium chlorochromate (2.4 gr, 11 mmol) in anhydrous CH2Cl2 (60 mL) was added a solution of the above alcohol in anh. CH2Cl2 and the reaction was heated under reflux for 5 hours. Upon completion, it was cooled to room temperature and poured into diethyl ether. The solution was then filtered through a pad of silica and concentrated under reduced pressure to yield 21 (2.4 gr, 95%). 20: white solid; 1H NMR (400 MHz, CDCl3) δ 10.15 (s, 1H), 8.31 (bs, 1H), 8.08 (bs, 1H), 7.98 (dd, 1H, J=1.5 Hz, J=8.5 Hz), 7.86 (m, 2H), 7.67 (dd, 1H, J=1.5 Hz, J=8.5 Hz); 13C NMR (100 MHz, CDCl3) δ 191.8, 137.3, 134.3, 134.1, 131.0, 131.0, 130.6, 130.2, 128.2, 124.0, 123.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe solution was then filtered through a pad of silica
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1ed9c1948d84bd6a4532946fd4b2398
Source dataset
uspto-grants-2015_01
Patent number
US08940918B2

Reaction notes

Loading…