Bromine → HCID 68856422, compound

HRID 226102Notes

Reaction equation

HRID 226102 reaction equation
[C:1]([C:5]1[C:10]2[S:11][C:12]([CH3:14])=[CH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:15]Br>C(Cl)Cl>[Br:15][C:13]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=2[S:11][C:12]=1[CH3:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 68856753HCID 68856753, compound

Product 1

HCID 68856422HCID 68856422, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-tert-butyl-2-methyl-benzo[b]thiophene 94.69 g, 23.0 mmol) in CH2Cl2 (100 mL) is cooled to 0° C. It is treated with Br2 (1.18 mL, 23.0 mmol). The resulting reaction mixture is stirred at rt overnight. It is washed with 10% Na2SO3 (2×50 mL); brine (50 mL); dried with Na2SO4, filtered and concentrated gives the title compound (4.99 g, 17.57 mmol, 76%). 1H NMR (CDCl3): δ 1.53 (s, 9H), 2.56 (s, 3H), 7.32 (dd, J=7.5, 1.3 Hz, 1H), 7.38 (t, J=7.5 Hz, 1H), 7.63 (dd, J=7.5 Hz, 1.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C13H15BrS (M+1)+: 284.2. found: 284.9.

Workup

  1. customThe resulting reaction mixture
  2. washIt is washed with 10% Na2SO3 (2×50 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78fa75f210754391b032ef5a9937c186
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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