Dimethyl Sulfide → 4-Cyano-3-fluorobenzyl bromide

HRID 278190

Reaction equation

HRID 278190 reaction equation
[Br:1]N1C(=O)CCC1=O.CSC.[F:12][C:13]1[CH:20]=[C:19]([CH2:21]O)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>C(Cl)Cl>[Br:1][CH2:21][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:12])[CH:20]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 27784664-Cyano-3-fluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (6.6 g, 0.037 mol) was dissolved in CH2Cl2 (150 mL), cooled to 0° C. and treated with dimethylsulfide (3.27 mL, 0.0446 mol). The solution was cooled to −20° C. and then treated dropwise with a solution of 2-fluoro-4-hydroxymethylbenzonitrile (3.74 g, 0.0248 mol) in CH2Cl2 (30 mL). After the addition, the reaction mixture was stirred at 0° C. for 2 h then left to warm to ambient temperature overnight. The reaction mixture was added to ice/H2O, extracted with EtOAc, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified by chromatography (silica gel, 5-10% EtOAc/hexane.

Workup

  1. temperatureThe solution was cooled to −20° C.
  2. additionAfter the addition
  3. waitthen left
  4. temperatureto warm to ambient temperature overnight
  5. extractionextracted with EtOAc
  6. customthe organic layer separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-889c81f0543f40ed914e44521fc7a8e3
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Linked notes

Loading…