Water → 3,4-Dihydroxy-5-(trifluoromethyl)benzoic acid

HRID 62779Notes

Reaction equation

HRID 62779 reaction equation
B(Br)(Br)Br.[OH:5][C:6]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:19]C.O>C(Cl)Cl>[OH:19][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:15]([F:16])([F:17])[F:18])[C:6]=1[OH:5])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 670417934-Hydroxy-3-methoxy-5-(trifluoromethyl)benzoic acid

Product 1

HCID 670415763,4-Dihydroxy-5-(trifluoromethyl)benzoic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (392 μL, 4.15 mmol) was added to a suspension of 4-hydroxy-3-methoxy-5-(trifluoromethyl)benzoic acid (4) (392 mg, 1.66 mmol) in DCM (10 mL) at 0° C. The reaction mixture was allowed to warm to RT and stirred for 70 h. The reaction mixture was cautiously added to stirring iced water (50 mL) and stirred for 10 min. The product was extracted with DCM (2×20 mL), and then the combined organic extracts were washed with brine (2×20 mL). The solvent was removed in vacuo and the residue was purified by silica chromatography (12 g, 0-10% MeOH in DCM) to afford 3,4-dihydroxy-5-(trifluoromethyl)benzoic acid (5) (257 mg, 68%) as a white solid: m/z 221 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.83 (1H, br s), 10.45 (2H, br d), 7.56 (2H, dd).

Workup

  1. additionThe reaction mixture was cautiously added
  2. stirringstirred for 10 min
  3. extractionThe product was extracted with DCM (2×20 mL)
  4. washthe combined organic extracts were washed with brine (2×20 mL)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica chromatography (12 g, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-7c55e024cf3b4a908a798dae98515257
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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