Tetrahydrofuran → 1-Bromo-4-fluoro-2,5-bis[(1-methoxy-1-methylethoxy)methyl]benzene

HRID 221919Notes

Reaction equation

HRID 221919 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][OH:12].[CH3:13][O:14][C:15]([CH3:17])=[CH2:16].[C:18](=[O:21])([O-])O.[Na+].O1C[CH2:26][CH2:25][CH2:24]1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:15]([CH3:17])([O:14][CH3:13])[CH3:16])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][O:12][C:25]([O:21][CH3:18])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 59278999(2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol

Product 1

HCID 594887661-Bromo-4-fluoro-2,5-bis[(1-methoxy-1-methylethoxy)methyl]benzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

(2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol (71.3 mg, 0.303 mmol) was dissolved in tetrahydrofuran (1 mL), and 2-methoxypropene (214.7 mg, 2.97 mmol) was added thereto. The resultant mixture was cooled to 0° C., and then p-toluenesulfonic acid (1.0 mg. 0.0029 mmol) was added thereto. This mixture was stirred for 40 minutes, and then saturated aqueous sodium hydrogen carbonate was added. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (111.7 mg, 97%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6bb24346a804e0f93bba34cd9f536cb
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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