Sodium Hydroxide → 5-(2-Bromothiazol-5-yl)-2-fluorobenzonitrile

HRID 1891493Notes

Reaction equation

HRID 1891493 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])(=O)C.[K+].[Br:20]Br.[OH-].[Na+]>C(O)(=O)C>[Br:20][C:13]1[S:14][C:10]([C:7]2[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517044Potassium AcetateHCID 671916142-Fluoro-5-(thiazol-5-yl)benzonitrile

Product 1

HCID 583673815-(2-Bromothiazol-5-yl)-2-fluorobenzonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirring solution of 2-fluoro-5-(thiazol-5-yl)benzonitrile THZ INT-3 (0.429 g, 2.1 mmol) in acetic acid (10.5 mL) was added potassium acetate (0.412 g, 4.2 mmol). Bromine (0.647 mL, 12.6 mmol) was added dropwise over 10 minutes and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was basified with 1N NaOH and washed with EA and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography (20% EA/Hexanes) to produce 0.10 g (30%) of 5-(2-bromothiazol-5-yl)-2-fluorobenzonitrile THZ INT-4. LCMS-ESI (m/z) calculated for C10H4BrFN2S: 283.1; found 284.9 [M+H]+, tR=3.33 min.

Workup

  1. washwashed with EA and brine
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (20% EA/Hexanes)

Sources & evidence

ORD record
ord-e7a34ec7474540249045f2bc11d63156
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

Loading…