Sulfuric Acid → 2,3-Dichloro-6-fluorobenzaldehyde

HRID 1789035Notes

Reaction equation

HRID 1789035 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[Cl:14].CN(C1C=CC=CC=1)[CH:17]=[O:18].S(=O)(=O)(O)O>O1CCCC1.CCOCC>[Cl:14][C:8]1[C:7]([Cl:6])=[CH:12][CH:11]=[C:10]([F:13])[C:9]=1[CH:17]=[O:18]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 66737N-MethylformanilideHCID 740281,2-Dichloro-4-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 32600622,3-Dichloro-6-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Butyl lithium (48 ml of 1.6M in hexane, 52.3 mmoles) was added with stirring over 1.5 hours under nitrogen to a solution of 1,2-dichloro-4-fluorobenzene (7.85 g, 47.6 mmoles) in dry tetrahydrofuran (120 ml) at -68°. The solution was stirred at -68° for 2 hours and then N-methyl-N-phenylformamide (6.48 ml) in dry tetrahydrofuran (15 ml) was added over 1.5 hours. After a further 1.5 hours at -68°, the reaction mixture was poured into 10% aqueous sulphuric acid and ether. The ethereal layer was separated, washed with brine, dried (Na2SO4) and evaporated to give the desired aldehyde (8 g). M+ 196/194/192, nmr (CDCl3)δ10.5 (s,H).

Workup

  1. waitAfter a further 1.5 hours at -68°
  2. customThe ethereal layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-aa32893fef904f078bce9e10111891da
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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