Dichloromethane → 2,2,2-Trifluoroethyl 5-bromonaphthalene-2-sulfonate

HRID 1473300Notes

Reaction equation

HRID 1473300 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12](Cl)(=[O:14])=[O:13])=[CH:7]2.C(Cl)Cl.[F:19][C:20]([F:24])([F:23])[CH2:21][OH:22].C(N(CC)CC)C>CCOC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:22][CH2:21][C:20]([F:24])([F:23])[F:19])(=[O:13])=[O:14])=[CH:7]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 64092,2,2-TrifluoroethanolHCID 8471TriethylamineHCID 109577165-bromonaphthalene-2-sulfonyl Chloride

Product 1

HCID 866873572,2,2-Trifluoroethyl 5-bromonaphthalene-2-sulfonateYield 41.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A round bottom flask was charged with 5-bromonaphthalene-2-sulfonyl chloride (5.00 g, 16.36 mmol) and CH2Cl2 (16.36 mL) was added. To this solution was added 2,2,2-trifluoroethanol (1.542 mL, 21.27 mmol) followed by triethylamine (3.42 mL, 24.54 mmol). The resulting solution was maintained at rt for 1 h and then concentrated. The residue was purified by MPLC using a silica gel column (80 g) using a 98:2 Heptane:EtOAc to 100% EtOAc gradient to afford 2,2,2-trifluoroethyl 5-bromonaphthalene-2-sulfonate (2.49 g, 6.75 mmol) as a white amorphous solid.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-34fd4d7fc45f4123859a5acd3712196f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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