Thionyl Chloride → 4-Bromo-N-(2-chloroethyl)-N-methylbenzenemethanamine

HRID 418615Notes

Reaction equation

HRID 418615 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[CH2:8][CH2:9]O)=[CH:4][CH:3]=1.O=S(Cl)[Cl:16]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[CH2:8][CH2:9][Cl:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58790142HCID 58790142, compound

Product 1

HCID 587903924-Bromo-N-(2-chloroethyl)-N-methylbenzenemethanamineYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 72 (2.9 g, 11.9 mmol) in toluene (20 ml) at RT was added SOCl2 (2.83 g, 2 eq, 23.8 mmol) and the mixture was heated to 60° C. for 3 hrs. The solvent was removed and the crude was dissolved in EtOAc then partitioned between water and satd NaHCO3 soln. The organic phase was collected, dried over Na2SO4, filtered and concentrated. The crude was purified by column chromatography (20% EtOAc in hexane) to afford 73 as a brown oil (2.9 g, 93% yield). 1H NMR (DMSO-d6) δ (ppm): 7.45 (m, 2H), 7.21 (m, 2H), 3.57 (t, J=6.85 Hz, 2H), 3.52 (s, 2H), 2.74 (t, J=6.85 Hz, 2H), 2.26 (s, 3H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe crude was dissolved in EtOAc
  3. customthen partitioned between water
  4. customThe organic phase was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-1edae68557424e3bb3e0c284ce47edef
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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