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

HRID 1276532Notes

Reaction equation

HRID 1276532 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 δ7.72 (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 (br s, 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-0df5965ff49c4ffdb52213cbd0310d10
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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