Sulfuric Acid → HCID 86639440, compound

HRID 1690221Notes

Reaction equation

HRID 1690221 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:26][CH2:27][O:28][CH3:29])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][C:12]=2[CH2:30][CH2:31][CH3:32])[CH:7]=[CH:6][C:5]=1C=C)C.[Br-:35].[Na+].[Br:37]([O-])(=O)=O.[Na+].S(=O)(=O)(O)O.O1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>>[Br:35][CH2:9][CH:4]([C:5]1[CH:6]=[C:7]([Br:37])[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:26][CH2:27][O:28][CH3:29])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][C:12]=2[CH2:30][CH2:31][CH3:32])=[CH:52][C:51]=1[O:50][CH2:49][CH3:48])[OH:3]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 253881Sodium BromideHCID 23668195Sodium BromateHCID 86639441HCID 86639441, compound

Product 1

HCID 86639440HCID 86639440, compoundYield 68%

Procedure

2-Ethoxy-4-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-1-vinylbenzene (53 mg, 0.108 mmol) was dissolved in dioxane (100 μL). The resultant was added with a mixed aqueous solution of sodium bromide (16 mg, 0.151 mmol) and sodium bromate (11 mg, 0.0753 mmol) (water 200 μL) at room temperature, and then added with concentrated sulfuric acid (6.4 μL, 0.118 mmol). The resultant mixture was stirred at room temperature for 3.5 hours and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium thiosulfate and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (n-hexane/ethyl acetate), and 2-bromo-1-{5-bromo-2-ethoxy-4-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-phenyl}-ethanol (49 mg, yield 68%) was obtained as a yellow oil.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium thiosulfate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-2c7af26cdc6c41adad2e89c4c690b40d
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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