3'-Bromoacetophenone → 2-(3-Bromophenyl)propan-2-ol

HRID 2196456Notes

Reaction equation

HRID 2196456 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1)=[O:3].[CH3:11][Mg]Br.[Cl-].[NH4+]>C(OCC)C.O1CCCC1.C(OCCCC)CCC>[Br:10][C:6]1[CH:5]=[C:4]([C:2]([OH:3])([CH3:11])[CH3:1])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 165023'-BromoacetophenoneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon stream, 6.5 g of 3-bromoacetophenone are placed in a round-bottomed flask and dissolved in 544 ml of diethyl ether and 272 ml of tetrahydrofuran. The mixture is cooled to 0° C. using an ice bath, and 100 ml of a 1M solution of methylmagnesium bromide in dibutyl ether are added thereto, dropwise. The mixture is stirred at 0° C. for 1 h and 400 ml of a saturated aqueous solution of ammonium chloride are added. The organic phase is separated, dried over magnesium sulphate and concentrated under reduced pressure. 10.0 g of compound are obtained. 1H NMR (DMSO-d6, δ in ppm): 1.45 (s, 6H); 5.15 (s, 1H); 7.25 (t, 1H); 7.4 (d, 1H); 7.45 (d, 1H); 7.65 (s, 1H).

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b045dd1ce6884783a0ad8783d49cafee
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

Loading…