Hydrochloric Acid → 1-(3-Bromophenyl)-2-methylpropan-1-ol

HRID 545243Notes

Reaction equation

HRID 545243 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].O1CCCC1.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16].Cl>O1CCCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]([OH:16])[CH:1]([CH3:3])[CH3:2])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 765833-BromobenzaldehydeHCID 178420664HCID 178420664, compound

Product 1

HCID 110855641-(3-Bromophenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With cooling with ice, 150 mL of 1.0 M isopropylmagnesium chloride/tetrahydrofuran solution was added to tetrahydrofuran (200 mL) solution of 21.9 g of 3-bromobenzaldehyde. 4 N hydrochloric acid was added to the reaction liquid, extracted with diethyl ether, and washed with saturated sodium hydrogencarbonate solution and saturated saline water in that order. This was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=19/1 to 4/1) to obtain 4.20 g of the entitled compound as an oily substance.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with saturated sodium hydrogencarbonate solution and saturated saline water in that order
  3. dry with materialThis was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=19/1 to 4/1)

Sources & evidence

ORD record
ord-92294b43e18249e182a2f37d2968c84b
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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