Sulfuric Acid → Methyl (2-bromo-4-fluorophenyl)acetate

HRID 1779010Notes

Reaction equation

HRID 1779010 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([OH:17])=[O:16].[C:18]([O-])([O-])=O.[Na+].[Na+]>CO>[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 34778092-Bromo-4-fluorophenylacetic acid

Product 1

HCID 25178031Methyl (2-bromo-4-fluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sulfuric acid (1.50 mL) was added cautiously to a solution of 2-bromo-4-fluorophenylacetic acid (1.00 g, 4.29 mmol) in MeOH (25 mL) and the resulting mixture stirred overnight at room temperature. Saturated aqueous Na2CO3 solution was added until the pH of the mixture was 14, then the aqueous layer was extracted with DCM (2×100 mL). The combined organics were dried over MgSO4 then the volatiles were removed in vacuo to yield the title compound A48 as a clear oil (1.00 g, 94%); 1H NMR (400 MHz, CDCl3) δ 7.34 (dd, J=8.2, 2.6 Hz, 1H), 7.29 (dd, J=8.5, 6.0 Hz, 1H), 7.03 (td, J=8.3, 2.6 Hz, 1H), 3.79 (s, 2H), 3.74 (s, 3H). LCMS-A: rt 5.911 min.

Workup

  1. extractionthe aqueous layer was extracted with DCM (2×100 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-d9d5d96e42ef450986c1fcc44f0dfebd
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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