Ammonium Chloride → 1-(7-Bromo-benzo[1,3]dioxol-5-yl)-2-methyl-propan-1-ol

HRID 460309

Reaction equation

HRID 460309 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[CH:13]([Mg]Cl)([CH3:15])[CH3:14].[Cl-].[NH4+]>CCOCC>[Br:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]([OH:12])[CH:13]([CH3:15])[CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 184453941-(7-Bromo-benzo[1,3]dioxol-5-yl)-2-methyl-propan-1-olYield 96.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-bromo-benzo[1,3]dioxole-5-carbaldehyde (437 mg, 1.91 mmol) in dry ether (6 mL) was added slowly under argon at −30° C. isopropylmagnesium chloride (1.15 mL, 2.0 M in ether, 2.29 mmol) and the solution stirred for 30 minute. A solution of aqueous ammonium chloride was added and the layers separated. The aqueous layer was extrated with ethyl acetate and the organic combined and washed with water, brine, dried (MgSO4), filtered and evaporated to give 503 mg of 1-(7-bromo-benzo[1,3]dioxol-5-yl)-2-methyl-propan-1-ol.

Workup

  1. customthe layers separated
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2cb68651744b4569b1e4bc0ac9ee3e60
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Linked notes

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