Hydrochloric Acid → 2-(5-Bromo-2-chlorophenyl)propan-2-ol

HRID 216272

Reaction equation

HRID 216272 reaction equation
COC(=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[Cl:11].[CH3:13][Mg]Br.Cl.C([O:19][CH2:20][CH3:21])C>C1COCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([Cl:11])=[C:4]([C:20]([OH:19])([CH3:21])[CH3:13])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 842098Methyl 5-bromo-2-chlorobenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 685596932-(5-Bromo-2-chlorophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-2-chloro-benzoic acid methyl ester (5 g) in diethyl ether (200 mL) cooled to −70° C. is added 3 M methylmagnesium bromide in THF (20 mL) dropwisely. The solution is stirred at −78° C. for 2 h and allowed to warm to room temperature for 16 hours. The solution is cooled to 0° C. and 1 N HCl (100 mL) is added dropwisely. The mixture is extracted with EtOAc (2×150 mL). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue is chromatographed on silica gel eluting with 20% EtOAc in heptane to afford 2-(5 bromo-2-chloro-phenyl)-propan-2-ol (4.56 g). MS: 250 (M+H); 1H NMR (300 MHz, CDCl3) □7.8 (m, 1H); 7.5 (m, 1H); 7.2 (m, 1H); 4.4 (s, 1H); 1.6 (s, 6H).

Workup

  1. temperatureto warm to room temperature for 16 hours
  2. temperatureThe solution is cooled to 0° C.
  3. extractionThe mixture is extracted with EtOAc (2×150 mL)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is chromatographed on silica gel eluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-7de35ea0c8994387bc7db0953ad1b8b3
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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