Water → HCID 55264110, compound

HRID 1879124Notes

Reaction equation

HRID 1879124 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:15])[C:9]([O:16]C)=[CH:8][CH:7]=1.O.[OH-].[Na+]>ClCCl>[Cl:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:15])[C:9]([OH:16])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 38560396-Chloro-2-fluoro-3-methoxybenzoic acid2×

Product 1

HCID 55264110HCID 55264110, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.5 ml, 15.3 mmol) was added dropwise to a solution of 6-chloro-2-fluoro-3-(methyloxy)benzoic acid (intermediate 33, 1.04 g, 5.1 mmol) in dichloromethane (100 ml) at 0° C. under an atmosphere of Argon. The reaction was stirred at room temperature for 18 hrs. Water (5 ml) was added and the solid formed stirred for 5 mins. Sodium hydroxide (2M, 4 ml) was added and the remaining solid dissolved. The layers were separated and the aqueous layer evaporated to afford a colourless solid. This was extracted with ethyl acetate (3×) and the combined organics evaporated to afford the title compound as a yellow solid (831 mg). 1H-NMR δ 7.02 (1H, t, J 10), 7.16 (1H, dd, J 10, 3), 10.48 (1H, s), 13.96 (1H, br s).

Workup

  1. customthe solid formed
  2. stirringstirred for 5 mins
  3. dissolutionthe remaining solid dissolved
  4. customThe layers were separated
  5. customthe aqueous layer evaporated
  6. customto afford a colourless solid
  7. extractionThis was extracted with ethyl acetate (3×)
  8. customthe combined organics evaporated

Sources & evidence

ORD record
ord-f1344d5673a4426cb47af1c5ce98ac19
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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