Water → HCID 59218422, compound

HRID 2246676Notes

Reaction equation

HRID 2246676 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.[Li]CCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:35])(=O)=O)=CC=1.O>C1COCC1>[F:35][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 588007N-FluorobenzenesulfonimideHCID 59218386HCID 59218386, compoundHCID 178418339Butyllithium

Product 1

HCID 59218422HCID 59218422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To stirring solution of bromide 47.5 (1.0 g, 3.1 mmol) in THF at −78° C. is added n-BuLi (1.6 M, 2.11 mL, 3.4 mmol), and stirring is continued for 1 hour. N-Fluorobenzene sulfonimide (3.7 mmol) is added and the mixture is allowed to warm to 23° C. Water is added to quench the reaction. The aqueous layer is extracted with EtOAc (3×100 mL), and the organic layer is dried over MgSO4 and concentrated in vacuo. The residue is purified by column chromatography (silica, EtOAc/Hexane), to afford fluoride 47.6.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous layer is extracted with EtOAc (3×100 mL)
  4. dry with materialthe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica, EtOAc/Hexane)

Sources & evidence

ORD record
ord-9fbe738cc30f4f38a3df7c90ddbac4e4
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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