Dimethyl Sulfide → 4-Cyano-3-fluorobenzyl bromide

HRID 1594843Notes

Reaction equation

HRID 1594843 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. then treated dropwise with a solution of 2-fluoro-4-hydroxymethylbenzonitrile, as described in Step C above, (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 after 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-0a1f05271c2844db85c30fa1302d098e
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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