Acetic Acid → HCID 57467610, compound

HRID 1662439Notes

Reaction equation

HRID 1662439 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8].C(Cl)Cl.C(O)(=O)C>CCOC(C)=O>[Br:1][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([F:3])[C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 24408BromineHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 57467610HCID 57467610, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Bromine (1.60 mL, 31.1 mmol) was added dropwise with stirring over 30 minutes to an ice-cooled solution of 66.49A (4.79 g, 28.1 mmol) in a 1:1 mixture of DCM (20 mL) and acetic acid (20 mL). Upon complete addition, the reaction mixture was allowed to warm to room temperature and monitored with TLC and LC-MS. After stirring at room temperature for 40 hours, the mixture was diluted with EtOAc, and then the resulting solution was washed twice with aqueous saturated Na2SO3, once with water, and once with brine. After drying over anhydrous magnesium sulfate, filtration, and concentration, the white solid 66.49B was obtained 6.69 g, 95% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.05 (1H, m), 7.75 (1H, dd, J=10.6, 2.0 Hz), 6.12 (1H, s), 3.94 (3H, s).

Workup

  1. additionUpon complete addition
  2. washthe resulting solution was washed twice with aqueous saturated Na2SO3, once with water
  3. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration

Sources & evidence

ORD record
ord-7f56325804ea430fbb2e6de4d3adb70a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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