Methanesulfonyl chloride → HCID 88920430, compound

HRID 525430Notes

Reaction equation

HRID 525430 reaction equation
[F:1][C:2]([F:18])([F:17])[CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[OH:4].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:4][CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[C:2]([F:17])([F:18])[F:1])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11230594HCID 11230594, compound

Product 1

HCID 88920430HCID 88920430, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(6-methoxynaphthalen-2-yl)ethanol (500 mg, 2 mmol) and TEA (610 mg, 6 mmol, 3 eq) in DCM (10 mL) was added MsCl (680 mg, 6 mmol, 2 eq) at 0° C. dropwise. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with sat. NaHCO3 (5 mL), washed with brine (5 mL*3), dried over Na2SO4 and concentrated to give 2,2,2-trifluoro-1-(6-methoxynaphthalen-2-yl)ethyl methanesulfonate (420 mg, yield: 65%) as a white solid. ESI-MS (M+1)+: 335.1. 1HNMR (400 MHz, CDCl3) δ: 7.90 (s, 1H), 7.83-7.78 (m, 2H), 7.54 (d, J=8.0 Hz, 1H), 7.22 (dd, J=8.4, 2.4 Hz, 1H), 7.16 (s, 1H), 5.90 (q, J=6.4 Hz, 1H), 3.94 (s, 3H), 2.93 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 (5 mL)
  2. washwashed with brine (5 mL*3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e60a6d6b146e40f0b71d24fded286781
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

Loading…