Water → alpha-Resorcylic acid, 4-chloro-

HRID 62767Notes

Reaction equation

HRID 62767 reaction equation
BrB(Br)Br.[Cl:5][C:6]1[C:16]([O:17]C)=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][C:7]=1[O:19]C.O>C(Cl)Cl>[Cl:5][C:6]1[C:16]([OH:17])=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[OH:19]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67041804HCID 67041804, compound

Product 1

HCID 3025235alpha-Resorcylic acid, 4-chloro-Yield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tribromoborane (318 μL, 3.29 mmol) was added dropwise to a solution of ethyl 4-chloro-3,5-dimethoxybenzoate (2) (115 mg, 0.470 mmol) in DCM (1.5 mL) at 0° C. and the mixture was stirred at the same temperature for 4 h. The reaction mixture was allowed to warm to RT and then poured cautiously in to iced water (5 mL). The mixture was extracted with EtOAc (3×5 mL), and the combined organic extracts were washed with brine (2×5 mL), dried over MgSO4 and evaporated in vacuo to give 4-chloro-3,5-dihydroxybenzoic acid (3) (72 mg, 78%) as a brown solid: m/z 187 [M−H]− (ES−).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×5 mL)
  2. washthe combined organic extracts were washed with brine (2×5 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0374790a6404952a61cc4468ef506f4
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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