Dimethylformamide → 10-Bromoanthracene-9-carbaldehyde

HRID 2413610Notes

Reaction equation

HRID 2413610 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([Br:16])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]CCCC.CN([CH:25]=[O:26])C>>[Br:16][C:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:2]([CH:25]=[O:26])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[CH:14]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 682269,10-DibromoanthraceneHCID 178418339Butyllithium

Product 1

HCID 60074310-Bromoanthracene-9-carbaldehyde

Procedure

This material was made from 9,10 dibromoanthracene (Eastman, 20 g, 60 mmol) modifying the procedure of R. Kuhn and H. Fischer, Chem. Ber. 94 3060 (1961). In this procedure, the reaction mixture was cooled to -78° before the nBuLi was added. The resulting mixture was warmed to RT over 1 H and then refluxed until the crystalline starting material disappeared. The mixture was then cooled to -78° again before the DMF was added (in one portion). The flask was warmed to RT and then quenched with 1M HBr (200 mL). The two-phase system was then extracted with CH2Cl2 (3×500 mL). The extracts combind, dried (MgSO4), filtered, and the solvent removed to give the crude material. This was purified by preparative HPLC using PhCH3 as the eluting solvent. After the solvent was removed 13.06 g (76%) of 10-bromo-9-anthracenecarbaldehye mp 215°-216.5°, (lit. mp 218°, P. Kuhn and H. Fischer, Chem. Ber. 94 3060 (1961)), (C,H,Br) was obtained.

Workup

  1. additionwas added
  2. temperaturerefluxed until the
  3. additionwas added (in one portion)
  4. temperatureThe flask was warmed to RT
  5. customquenched with 1M HBr (200 mL)
  6. extractionThe two-phase system was then extracted with CH2Cl2 (3×500 mL)
  7. dry with materialThe extracts combind, dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-6130805c46bf49e1abf9e596ced7a096
Source dataset
uspto-grants-1988_01
Patent number
US04719047

Reaction notes

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