Bromine → 4,5-Dibromo-2-phenyl-1,3-thiazole

HRID 589235Notes

Reaction equation

HRID 589235 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][CH:3]=1.[Br:13]Br>C(Cl)(Cl)Cl>[Br:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:6][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 135466495-Bromo-2-phenyl-1,3-thiazole2×

Product 1

HCID 135466504,5-Dibromo-2-phenyl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Compound 18 (5.0 g, 21 mmol) was dissolved in CHCl3 (250 mL). Br2 (16.7 g, 105 mmol) was dissolved in CHCl3 (50 mL) and added to the solution of 18 via addition funnel over 10 minutes. The reaction mixture stirred at room temperature for 5.5 hours; then was transferred to a 1 L separatory funnel and washed with Na2S2O3 (3×100 mL) followed by brine (2×150 mL). The organic fractions were dried over MgSO4 and concentrated. The crude product was purified by column (2:1 hexanes/CHCl3). 1H NMR (600 MHz, CDCl3) δ 7.85 (d, J=7.3, 2H), 7.50-7.40 (m, 3H).

Workup

  1. customthen was transferred to a 1 L separatory funnel
  2. washwashed with Na2S2O3 (3×100 mL)
  3. dry with materialThe organic fractions were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column (2:1 hexanes/CHCl3)

Sources & evidence

ORD record
ord-d0932bc90e554752902100b779c2e807
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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