Triethylamine → HCID 68857012, compound

HRID 226056Notes

Reaction equation

HRID 226056 reaction equation
[Br:1][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12](O)([CH3:14])[CH3:13])[C:4]=2[S:5][C:6]=1[CH3:7].CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([CH3:14])=[CH2:13])[C:4]=2[S:5][C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68857784HCID 68857784, compound

Product 1

HCID 68857012HCID 68857012, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-bromo-2-methyl-benzo[b]thiophen-7-yl)-propan-2-ol (0.98 g, 3.45 mmol) in CH2Cl2 910 mL) is treated with Et3N (0.72 mL, 5.18 mmol) and MsCl (0.29 mL, 3.80 mmol) at) 0° C. The reaction is stirred at 0° C. for 10 min, and at RT overnight. It is diluted with EtOAc (50 mL), washed with 0.1 M HCl (10 m), H2O (20 mL); dried with Na2SO4, filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.36 g, 1.35 mmol, 39%). 1H NMR (CDCl3): δ) 2.23 (s, 3H), 2.56 (s, 3H), 5.40 (s, 1H), 5.49 (s, 1H), 7.28 (s, 1H), 7.41 (t, J=7.1 Hz, 1H), 7.64 (d, J=7.9 Hz, 1H) ppm.

Workup

  1. customat RT
  2. customovernight
  3. washwashed with 0.1 M HCl (10 m), H2O (20 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-0ee86a4ff5f3462f8ade54b85e48ac0b
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

Loading…