Benzyl Bromide → Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

HRID 1623657Notes

Reaction equation

HRID 1623657 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:9][C:10]1[CH:19]=[CH:18][C:17]([O:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([S:21]([O:20][C:17]2[CH:18]=[CH:19][C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 15727852Methyl 2-hydroxy-5-{[(4-methylphenyl)sulfonyl]oxy}benzoate

Product 1

HCID 86762539Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

Procedure

(Bromomethyl)benzene (3.81 g, 22.26 mmol) was added to methyl 2-hydroxy-5-{[(4-methylphenyl)sulfonyl]oxy}benzoate (may be prepared as described in Description 36; 2.87 g, 8.90 mmol) and the resulting mixture was refluxed overnight. After cooling, the resulting precipitate was filtered and the filtrate was evaporated. The crude product was purified by silica gel chromatography, eluting with a 4:1 mixture of hexane:ethyl acetate to yield the title compound as a colourless oil. 2.7 g.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was filtered
  4. customthe filtrate was evaporated
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a 4:1 mixture of hexane

Sources & evidence

ORD record
ord-d37e0a2dd1dd45afb5713aa859ab0eda
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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