Hydrochloric Acid → 1-Bromo-4-(7-methoxyheptylthio)benzene

HRID 1977285

Reaction equation

HRID 1977285 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br)=[CH:4][CH:3]=1.[CH3:17][O-:18].[Na+].Cl>CO.CCC(C(OCCN1C(C)C(C2C=CC=CC=2)OCC1)=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:18][CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 219974831-Bromo-4-(7-bromoheptylthio)benzene

Product 1

HCID 219975631-Bromo-4-(7-methoxyheptylthio)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 20395FenbutrazateSolvent

Procedure

To a solution of 1-bromo-4-(7-bromoheptylthio)benzene (5 g) in methanol (25 ml) was added 28% sodium mehtylate in nethanol (7.9 g) and the mixture was stirred under refluxing for 2 hours. The residue was adjusted to pH 2 with dilute HCl aq. and extracted with ethyl acetate. The organic layer was seperated, wahsed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (50:1) to give 1-bromo-4-(7-methoxyheptylthio)benzene (3.59 g).

Workup

  1. temperatureunder refluxing for 2 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was seperated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-3922bb71b3ae40dc9c6c6221f25629ac
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Linked notes

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