Thionyl Chloride → Methyl 4-bromo-2-chloro-5-fluorobenzoate

HRID 1849508Notes

Reaction equation

HRID 1849508 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:12])[CH:3]=1.S(Cl)(Cl)=O.[C:17](=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([Cl:12])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27362254-Bromo-2-chloro-5-fluorobenzoic acid

Product 1

HCID 44203099Methyl 4-bromo-2-chloro-5-fluorobenzoateYield 155.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2-chloro-5-fluorobenzoic acid (25.40 g, 100.00 mmol) in methanol (300 mL) was added thionyl chloride (0.8 mL, 11.00 mmol) over 5 min at 0° C. The reaction mixture was heated to reflux for 8 h and then neutralized by slow addition of sodium bicarbonate (5.0 g) at 0° C. The solid was filtered out and washed with ethyl acetate (50 mL), the combined filtrate was concentrated in vacuo to afford the title compound as a pale yellow solid (24.7 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.68-7.60 (m, 2H), 3.91 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationThe solid was filtered out
  4. washwashed with ethyl acetate (50 mL)
  5. concentrationthe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-23ebb30648d943a783fd7a521c886883
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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