Benzene → HCID 21692926, compound

HRID 449099Notes

Reaction equation

HRID 449099 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].S(Cl)(Cl)=O.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:8])=[CH:4][C:3]=1[F:11]

Participants

7

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 27733414-Bromo-3-fluorobenzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21692926HCID 21692926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an oven dried flask was added 4-bromo-3-fluorobenzoic acid (1.0 g, 0.0046 mol), thionyl chloride (0.65 mL, 0.0089 mol) and a drop of DMF and the reaction was refluxed for 2 h. The thionyl chloride was then distilled off and benzene (20 mL, 0.2 mol) and aluminum trichloride (0.576 g, 0.00432 mol) was added to the reaction mixture and the reaction was stirred at room temp for 1 h. The crude reaction mixture was poured onto ice and conc. HCl (15 mL). The organic layer was separated and the aqueous layer extracted with EtOAc. The combined organic phases were washed with 5% aq NaOH solution, water and dried (Na2SO4). The organic phase was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 2% EtOAc in hexane. 1H NMR (400 MHz, CDCl3): δ=7.45-7.55 (m, 3H), 7.58 (dd, J=8.84, 1.77 Hz, 1H), 7.60-7.66 (m, 1H), 7.70 (dd, J=8.21, 6.69 Hz, 1H), 7.75-7.82 (m, 2H).

Workup

  1. customIn an oven dried flask
  2. distillationThe thionyl chloride was then distilled off
  3. customThe crude reaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with EtOAc
  6. washThe combined organic phases were washed with 5% aq NaOH solution, water
  7. dry with materialdried (Na2SO4)
  8. concentrationThe organic phase was concentrated in vacuo
  9. customto give a residue which
  10. customwas purified by silica gel chromatography
  11. washeluting with 2% EtOAc in hexane

Sources & evidence

ORD record
ord-d86b7358ae9e44c6881f40a01054fa62
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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