Dimethylformamide → 4-Bromo-1-naphthaldehyde

HRID 1372138Notes

Reaction equation

HRID 1372138 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:21]=[O:22])C>CCOCC>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH:21]=[O:22])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 665211,4-DibromonaphthaleneHCID 178418339Butyllithium

Product 1

HCID 46404134-Bromo-1-naphthaldehydeYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 150 ml flask was added 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) and anhydrous ether (50 ml). After cooling to 0° C. n-BuLi (3.1 ml of 2.5 M in hexanes, 7.7 mmol) was added dropwise and stirred for 20 minutes after which anhydrous DMF (1.62 ml, 21 mmol) was added. The reaction was then warmed to ambient temperature and after 1 h the reaction was quenched with water (10 ml), stirred for 10 minutes, and extracted with ether (3×). The ether layer was dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to afford 1.02 g (62%) of product as a pure off-white solid: 1H NMR (300 MHz, DMSO-d6): δ 7.80–7.85 (2H, m), 8.10 (1H, d, J=7.7 Hz), 8.20 (1H, d, J=7.7 Hz), 8.32 (1H, m). 9.24 (1H, m), 10.42 (1H, s).

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customwas quenched with water (10 ml)
  4. extractionextracted with ether (3×)
  5. dry with materialThe ether layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a15ac5abb0f848ecbde4baf554053596
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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