Triethylamine → HCID 66893102, compound

HRID 516867Notes

Reaction equation

HRID 516867 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:13]O)[CH:9]=[CH:10][C:11]=1[F:12].C(N(CC)CC)C.S([Cl:31])(C)(=O)=O>C(Cl)Cl>[Cl:31][CH2:13][C:8]1[CH:9]=[CH:10][C:11]([F:12])=[C:6]([CH:7]=1)[O:5][CH2:4][C:3]1[C:2]([CH3:1])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66875369HCID 66875369, compound

Product 1

HCID 66893102HCID 66893102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-(2,6-dimethylbenzyloxy)-4-fluorophenyl)methanol (Step B, 3.7 g, 14.21 mmol), triethylamine (5 g, 50 mmol) in CH2Cl2 (50 ml) was added mesyl chloride (10.34 g, 90.2 mmol) at 0° C. under argon. The reaction mixture was stirred for 6 hours, washed with 10% Na2CO3, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hexane:ethyl acetate, 5:1) to give the title compound.

Workup

  1. washwashed with 10% Na2CO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (hexane:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-2bcc0508033140598246c6f3168b9dc9
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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