Hydrochloric Acid → 2-(3-Bromophenyl)propan-2-ol

HRID 2303585Notes

Reaction equation

HRID 2303585 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)=[O:6].O.Cl>C(OCC)C>[Br:13][C:9]1[CH:8]=[C:7]([C:5]([OH:6])([CH3:1])[CH3:4])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 165023'-BromoacetophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 150723832-(3-Bromophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of methylmagnesium-bromide (60 mL of a 3.0 M solution in diethyl ether) at 0° C. was added dropwise a solution of 3-bromoacetophenone (29.8 grams) in 75 mL of diethyl ether. Once the addition was complete, the mixture was stirred for 0.5 hours and poured into water. The aqueous phase was acidified with 1M hydrochloric acid and extracted with three portions of diethyl ether. The combined ether layers were washed with saturated sodium bicarbonate, concentrated to afford 30.4 grams of the title compound. 1H NMR δ 7.72 (br s, 1), 7.49 (d, 1, J=7.8), 7.37 (d, 1, J=7.9), 7.25 (dd, 1, J=7.8, 7.9), 4.19 (s, 1), 1.50 (brs, 6).

Workup

  1. additionOnce the addition
  2. extractionextracted with three portions of diethyl ether
  3. washThe combined ether layers were washed with saturated sodium bicarbonate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-646884486aa54b8e994753dc9b371698
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

Loading…