Dimethylformamide → 2-Fluorobiphenyl-4-carboxaldehyde

HRID 882951

Reaction equation

HRID 882951 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.C([Li])CCC.CN([CH:23]=[O:24])C>O1CCCC1>[F:14][C:4]1[CH:3]=[C:2]([CH:23]=[O:24])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 178418339Butyllithium

Product 1

HCID 27590832-Fluorobiphenyl-4-carboxaldehydeYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Bromo-2-fluoro-biphenyl (2 gm, 8 mmole) was dissolved in 20 ml of anhydrous tetrahydrofuran, THF, cooled to −78° C. under argon (Ar), n-Butyl lithium 2.5 M (3.5 ml, 8.8 mmole) was added drop wise over 10 min, and was stirred for additional 1 hr, DMF anhydrous (0.68 ml, 8.8 mmole) was then added, stirred for additional 1 hr, then warmed to room temperature over 4 hr, It was then quenched with water, extracted with ether, ether was dried, evaporated, the produced compound was purified using 9:1 hexane/ethyl acetate, to produce white solid (1 gm, 62.5%); H1-NMR INOVA-500 (CDCl3) δ 7.416-7.495 (m, 3H), 7.581-7.661 (m, 4H), 7.723 (d, J=8.0 Hz, 1H), 9.991 (s, 1H).

Workup

  1. stirringstirred for additional 1 hr
  2. customIt was then quenched with water
  3. extractionextracted with ether, ether
  4. customwas dried
  5. customevaporated
  6. customthe produced compound was purified

Sources & evidence

ORD record
ord-38ce749e115a4e8a9a2aee885400e139
Source dataset
uspto-grants-2012_08
Patent number
US08236799B2

Linked notes

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