Triethylamine → 4-Fluoro-N-[4-(methylthio)phenyl]benzenemethanamine

HRID 1789651Notes

Reaction equation

HRID 1789651 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>ClCCl>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:7][C:6]2[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660384-(Methylthio)anilineHCID 680214-Fluorobenzyl bromide

Product 1

HCID 220362054-Fluoro-N-[4-(methylthio)phenyl]benzenemethanamineYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5.0 mL (40.19 mmol) of 4-(methylthio)aniline and 8.4 mL (60.28 mmol) triethylamine dissloved in 30 mL dichloromethane was added 5.0 mL (40.19 mmol) 4-fluorobenzyl bromide. The mixture was stirred at room temperature for 12 h, partitioned between dichloromethane and sat. aqueous ammonium chloride, dried over MgSO4 and concentrated. Purification by column chromatography, eluting with ethyl acetate/hexane, provided 3.10 g of 4-[(4-fluorobenzyl)amino]thioanisole, along with recovered starting material.

Workup

  1. custompartitioned between dichloromethane and sat. aqueous ammonium chloride
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by column chromatography
  5. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-3d744372890e4a39aa80023067573048
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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