Bromine → 6-Bromo-4,4,7-trimethylthiochroman

HRID 2417339Notes

Reaction equation

HRID 2417339 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.[Br:14]Br.C(=O)(O)[O-].[Na+]>[Fe].ClCCl>[Br:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH3:12])[S:5][CH2:4][CH2:3][C:2]2([CH3:13])[CH3:1]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 10797842HCID 10797842, compound

Product 1

HCID 156611176-Bromo-4,4,7-trimethylthiochroman

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

6.2 g (32.2 mmol) of 4,4,7-trimethylthiochroman, 40 ml of dichloromethane and 90 mg of iron powder are introduced into a three-necked flask. 1.65 ml (32.2 mmol) of bromine are added and the mixture is stirred at room temperature for two hours. The reaction medium is poured into sodium bicarbonate solution and extracted with dichloromethane, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with heptane. 5.9 g (67%) of the bromo derivative are collected in the form of a pale yellow oil.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with heptane
  8. custom5.9 g (67%) of the bromo derivative are collected in the form of a pale yellow oil

Sources & evidence

ORD record
ord-bcd2f96ac7cd4b218e1fae9e8c540db6
Source dataset
uspto-grants-2004_11
Patent number
US06825360B1

Reaction notes

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