Ammonium Chloride → (4-Bromophenyl)(cyclopropyl)methanol

HRID 2407466Notes

Reaction equation

HRID 2407466 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg:5].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([Mg:5][Br:6])[CH2:3][CH2:2]1.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([CH:1]2[CH2:3][CH2:2]2)[OH:12])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 78037BromocyclopropaneHCID 5462224Magnesium

Product 2

HCID 123566(4-Bromophenyl)(cyclopropyl)methanolHCID 178418630HCID 178418630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Solution of cyclopropyl magnesium bromide is prepared from cyclopropyl bromide (12 g, 0.099 mol) and magnesium turnings (3.0 g, 0.123 mol) in tetrahydrofuran (60 mL) by using standard Grignard reaction procedure. This reagent solution is cooled to 5° C. and a solution of 4-bromobenzaldehyde (15.0 g, 0.081 mol) in tetrahydrofuran (30 mL) is added to it over a period of 15 minute at 10-15° C. The reaction mixture is treated with aqueous ammonium chloride solution and extracted with ethyl acetate (50 mL). The organic layer is concentrated under reduced pressure and the residue is purified by column chromatography (silica gel 230-400 mesh) to give (4-bromophenyl)-cyclopropylmethanol.

Workup

  1. customGrignard reaction procedure
  2. extractionextracted with ethyl acetate (50 mL)
  3. concentrationThe organic layer is concentrated under reduced pressure
  4. customthe residue is purified by column chromatography (silica gel 230-400 mesh)

Sources & evidence

ORD record
ord-a9f351773ab4489db23c7d916144ab73
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

Loading…