Water → HCID 89405922, compound

HRID 516207Notes

Reaction equation

HRID 516207 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([C:8](=[O:12])[CH2:9][CH2:10][I:11])[CH:5]=[CH:6][CH:7]=1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]([OH:12])[CH2:9][CH2:10][I:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 90199970HCID 90199970, compound

Product 1

HCID 89405922HCID 89405922, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Chloro-2-fluorophenyl)-3-iodopropan-1-one: To a solution of sodium iodide (165 mg, 1.099 mmol) in ACN (1 mL) was added chlorotrimethylsilane (0.139 mL, 1.099 mmol) dropwise. To the mixture was added water (0.016 mL, 0.916 mmol), followed by Intermediate 16B (169 mg, 0.916 mmol) in 1 mL ACN. After 15 min, the reaction mixture was diluted with EtOAc and washed with water followed by 10% Na2S2O3. The organic layer was then washed with brine and dried over MgSO4. The desired product was isolated as a yellow solid (286 mg, 100%). MS (ESI) m/z: 312.9 (M+2+H)+.

Workup

  1. washwashed with water
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-03e62ff3085b48f7970bd0907bfe8481
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

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