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

HRID 1630376Notes

Reaction equation

HRID 1630376 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-d90bdc1f5dfc4b5ebd478df3bf998975
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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