Diethyl Ether → 1-(4-Bromophenyl)-2-methylpropan-2-ol

HRID 1858319Notes

Reaction equation

HRID 1858319 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]C(OCC)=O)=[CH:4][CH:3]=1.[CH3:14][Mg]Br.[Cl-].[NH4+].C([O:21][CH2:22][CH3:23])C>C1(C)C=CC=CC=1.O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:22]([CH3:23])([OH:21])[CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 178418573HCID 178418573, compound

Product 1

HCID 3167851-(4-Bromophenyl)-2-methylpropan-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4 g (16.5 mmol) of ethyl 4-bromophenylacetate in 60 ml of diethyl ether was treated with 26 ml (36.4 mmol) of a 1.4M solution of methylmagnesium bromide in toluene/tetrahydrofuran (3:1) and the mixture heated at 40° C. for 1 hour and then cooled. 100 ml of saturated aqueous ammonium chloride were added and the phases separated. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 3.5 g (93%) of 1-(4-bromophenyl)-2-methyl-propan-2-ol as a colorless oil. [Mass spectrum (ESI) MH+ =229].

Workup

  1. temperaturecooled
  2. customthe phases separated
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-12c9cad0a7154f86be8bf8921720adc5
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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