Boron tribromide → Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate

HRID 2177725Notes

Reaction equation

HRID 2177725 reaction equation
B(Br)(Br)Br.[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26]C)[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([OH:26])[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2×

Product 1

HCID 67108192Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M solution in DCM, 5.85 ml) was added dropwise to a stirred, cooled solution of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 2.3 g) in dry DCM (45 ml) at −70° C. The resultant mixture was stirred at −70° C. for 40 minutes, then allowed to warm to room temperature. It was stirred at room temperature for 2 hours then poured into sodium bicarbonate (saturated aqueous solution). The layers were separated and the aqueous layer was extracted with further DCM. The combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (1.64 g) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with further DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9b388b3b5dff40f0b2e05f1f08aa39c7
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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