Hydrochloric Acid → 1-Bromo-2-(2,2-dimethoxypropyl)benzene

HRID 445358Notes

Reaction equation

HRID 445358 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:11])[CH3:10].[CH:12](OC)(OC)[O:13]C.Cl.O1CCOC[CH2:21]1.CCN(C(C)C)C(C)C>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:13][CH3:12])([O:11][CH3:21])[CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 27340921-(2-Bromophenyl)propan-2-one

Product 1

HCID 595364291-Bromo-2-(2,2-dimethoxypropyl)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromophenylacetone (4.45000 g, 21 mmol) was dissolved in 10 mL MeOH and trimethyl orthoformate (11 mL, 104 mmol) and hydrogen chloride, 4.0M solution in 1,4-dioxane (5.2 mL, 21 mmol) were added. The mixture was stirred for 1 h and neutralized carefully with DIEA (pH 7). The mixture was evaporated and filtered through a plug of silica providing 1-bromo-2-(2,2-dimethoxypropyl)benzene as a colorless liquid.

Workup

  1. customThe mixture was evaporated
  2. filtrationfiltered through a plug of silica

Sources & evidence

ORD record
ord-23781c5df85b49ce81363cf3768034e1
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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