Hydrochloric Acid → 2-Bromo-α-ethyl-4-fluorobenzenemethanol

HRID 558119Notes

Reaction equation

HRID 558119 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].O.Cl>C(OCC)C>[Br:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH:8]([OH:9])[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 574450672-Bromo-α-ethyl-4-fluorobenzenemethanolYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add ethylmagnesium bromide (1 M in ether, 8.37 mL, 8.37 mmol) at 0° C. under nitrogen to a solution of 2-bromo-4-fluorobenzaldehyde (1 g, 4.93 mmol) in diethyl ether (15 mL). Stir the mixture for 1 h at RT. Add water slowly followed by adjusting the mixture to acidic conditions with 2 M HCl. Extract the product with chloroform/IPA (3/1). Dry over sodium sulfate. Concentrate the solution in vacuo to a yellow oil. Purify by column chromatography (30% ethyl acetate in hexane) to give the title compound as a colorless oil (1.1 g, 96%). 1H NMR (400 MHz, CD3Cl) δ 0.99 (t, J=7.2 Hz, 3H), 1.75 (m, 2H), 4.99 (m, 1H), 7.03 (m, 1H), 7.25 (m, 1H), 7.53 (m, 1H).

Workup

  1. extractionExtract the product with chloroform/IPA (3/1)
  2. dry with materialDry over sodium sulfate
  3. concentrationConcentrate the solution in vacuo to a yellow oil
  4. customPurify by column chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7b7874bc08e14135a048edd9622caffe
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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