Hydrochloric Acid → HCID 57975908, compound

HRID 2388954Notes

Reaction equation

HRID 2388954 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:14][Mg]Br.C(OCC)(=O)C.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([OH:13])[CH3:14])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10800370HCID 10800370, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57975908HCID 57975908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (4.1 mmol) of 5-bromo-3-formyl-2-hydroxy-benzoic acid was dissolved in 100 mL of anhydrous THF under nitrogen. The solution was cooled in an ice-bath and 13.6 ml of a 3 M solution of methyl magnesium bromide was added. The mixture was stirred for 16 h, slowly warming to room temperature. The resulting solution was distributed between ethyl acetate and dilute aqueous hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and evaporated to afford 1.09 g of 5-bromo-2-hydroxy-3-(1-hydroxy-ethyl)-benzoic acid as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 7.76 (d, 1H), 7.72 (d, 1H), 4.98 (q, 1H), 1.30 (d, 3H), MS: m/z 258.9+261.0 (M+H+).

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9799cc5f15df4e7798a954b7515dad9a
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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