Bromine → HCID 68856390, compound

HRID 226055Notes

Reaction equation

HRID 226055 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]2[S:11][C:12]([CH3:14])=[CH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Br:15]Br>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10]2[S:11][C:12]([CH3:14])=[C:13]([Br:15])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 24408BromineHCID 53739261HCID 53739261, compound

Product 1

HCID 68856390HCID 68856390, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-benzo[b]thiophene-7-carboxylic acid methyl ester (0.50 g, 2.44 mmol) in CHCl3 (10 mL) is cooled to 0° C., treated with a solution of Br2 (0.13 mL, 2.44 mmol) in CHCl3 (5 mL). The reaction is stirred at 0° C. for 30 min, then at RT overnight. The reaction is diluted with CH2Cl2 (50 mL), washed with 10% Na2S2O3 (2×20 mL); dried with Na2SO4, filtered and concentrated to give the title compound (0.69 g, 2.43 mmol, 100%). 1H NMR (CDCl3): δ 2.58 (s, 3H), 4.02 (s, 3H), 7.50 (t, J=7.9 Hz, 1H), 7.92 (d, J=7.9 Hz, 1H), 8.08 (d, J=7.5 Hz, 1H).

Workup

  1. customat RT
  2. customovernight
  3. washwashed with 10% Na2S2O3 (2×20 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d031c273f83445fe94cba0d4661ebdc7
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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