1-Bromo-4-(diethoxymethyl)benzene → HCID 57592497, compound

HRID 1784405Notes

Reaction equation

HRID 1784405 reaction equation
[Mg].C(O[CH:5]([O:13]CC)[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)C.[CH3:16][O:17][C:18]1[C:19]([S:30](F)(=[O:32])=[O:31])=[CH:20][C:21]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23][C:22]=2[CH:29]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1.O>[CH3:16][O:17][C:18]1[C:19]([S:30]([C:9]2[CH:8]=[CH:7][C:6]([CH:5]=[O:13])=[CH:11][CH:10]=2)(=[O:32])=[O:31])=[CH:20][C:21]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23][C:22]=2[CH:29]=1

Participants

7

Reactant 4

HCID 6883401-Bromo-4-(diethoxymethyl)benzeneHCID 5462224MagnesiumHCID 9855836Potassium sodium tartarateHCID 57592494HCID 57592494, compound

Product 1

HCID 57592497HCID 57592497, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (1.4 g) in tetrahydrofuran (10 mL) were stirred under an atmosphere of argon and treated with a solution of 4-bromobenzaldehyde diethyl acetal (15.5 g) in tetrahydrofuran (60 mL) The mixture was stirred for 4 hours then the sulfonyl fluoride D4 (5.46 g) was added and the mixture was stirred for 60 hours. The mixture was poured into a solution of potassium sodium tartrate in water and extracted with ethyl acetate. The residue was purified by column chromatography 0-10% methanol (containing 0.5% aqueous ammonia)-dichloromethane. The product was treated with hydrochloric acid (10 mL) in tetrahydrofuran (100 mL) for 18 hours. The solution was basified and extracted with dichloromethane, and solvent evaporation gave the title compound D11 as a white solid. 1H NMR: δ CDCl3 2.38 (3H, s), 2.6 (4H, m), 2.9 (4H, m), 3.73 (3H, s) 6.65 (1H, s), 7.86 (1H, s), 8.02 (2H, d) 8.12 (2H, d), 10.12 (1H, s).

Workup

  1. stirringthe mixture was stirred for 60 hours
  2. extractionextracted with ethyl acetate
  3. customThe residue was purified by column chromatography 0-10% methanol (containing 0.5% aqueous ammonia)-dichloromethane
  4. additionThe product was treated with hydrochloric acid (10 mL) in tetrahydrofuran (100 mL) for 18 hours
  5. extractionextracted with dichloromethane, and solvent evaporation

Sources & evidence

ORD record
ord-d1982c7754cb4989a741bba95f1a126f
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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