Sodium Chloride → HCID 57467610, compound

HRID 2094761Notes

Reaction equation

HRID 2094761 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-c50b2eb27ed94f47ba5390ce9c37865d
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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