Sodium Chloride → HCID 57467610, compound

HRID 521534Notes

Reaction equation

HRID 521534 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([F:13])[CH:7]=1.C(OC)(=O)C.S([O-])([O-])=O.[Na+].[Na+].[Cl-].[Na+]>C(Cl)Cl.C(O)(=O)C.O>[CH3:3][O:4][C:5](=[O:14])[C:6]1[CH:7]=[C:8]([F:13])[C:9]([OH:12])=[C:10]([Br:1])[CH:11]=1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 6584Methyl AcetateHCID 24408BromineHCID 24437Sodium SulfiteHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 57467610HCID 57467610, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

During 30 min, 5.64 g (35.27 mmol) of bromine were added to a solution of 5.00 g (29.39 mmol) of 3-fluoro-4-hydroxy-benzoic acid methyl ester in 30 ml of DCM and 30 ml of acetic acid at 0° C. After stirring overnight, 200 ml of methyl acetate were added. The resulting solution was extracted with a solution of 7.56 g (60 mmol) of sodium sulfite in 50 ml of water, a saturated sodium chloride solution and water. The organic phase was dried over sodium sulfate, filtered and evaporated. The resulting white solid (7.2 g) was used in the next step without further purification.

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. filtrationfiltered
  3. customevaporated
  4. customThe resulting white solid (7.2 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-59bd07b0164a4532950e03b82be06beb
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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