Water → Ethyl 2-bromo-5-hydroxybenzoate

HRID 1049503Notes

Reaction equation

HRID 1049503 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCCCCCC.[Br:18][C:19]1[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].O>C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 81951-DodecanethiolHCID 6451240Aluminum(III) ChlorideHCID 43389585Ethyl 2-bromo-5-methoxybenzoate

Product 1

HCID 53487920Ethyl 2-bromo-5-hydroxybenzoateYield 91.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Aluminum chloride (11.0 g) was added to toluene (80 mL) at room temperature. 1-Dodecanethiol (33.5 g) was added at 0° C., and the mixture was stirred for 30 min. A solution of ethyl 2-bromo-5-methoxybenzoate (5.36 g) in toluene (40 mL) was added at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water in an ice bath, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.66 g) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-50e3ae022f74426981ff996805576f2b
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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