Bromine → HCID 131733707, compound

HRID 707457Notes

Reaction equation

HRID 707457 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[NH:8][C:9](=[O:12])[O:10][CH3:11])#[N:2].[Br:13]Br>C(O)(=O)C>[Br:13][C:6]1[S:5][C:4]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[C:3]([C:1]#[N:2])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 14015027HCID 14015027, compound

Product 1

HCID 131733707HCID 131733707, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound methyl 3-cyanothiophen-2-ylcarbamate (11.5 g, 63 mmol) in acetic acid (500 mL) was added bromine (12 g, 75 mmol) at room temperature. The solution was heated at 60° C. with stifling for 1 hour and then concentrated and treated with water (500 mL). It was extracted with ethyl acetate (3×300 mL) and the combined extracts were dried over sodium sulfate and concentrated to give 14 g (89%) of methyl 5-bromo-3-cyanothiophen-2-ylcarbamate as a solid. 1H NMR 400 MHz CDCl3 δ 3.89 (s, 3H), 6.90 (s, 1H), 8.05 (s, 1H).

Workup

  1. concentrationconcentrated
  2. additiontreated with water (500 mL)
  3. extractionIt was extracted with ethyl acetate (3×300 mL)
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-810fb36799be43dd8d5533619ed17ac6
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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