Trifluoroacetic acid → 2-Iodo-4-(pyrimidin-2-ylmethyl)phenol

HRID 2075224Notes

Reaction equation

HRID 2075224 reaction equation
[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:18].[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:18][C:30]1[CH:31]=[C:26]([CH2:25][C:20]2[N:21]=[CH:22][CH:23]=[CH:24][N:19]=2)[CH:27]=[CH:28][C:29]=1[OH:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 227684204-(Pyrimidin-2-ylmethyl)phenol

Product 1

HCID 584152472-Iodo-4-(pyrimidin-2-ylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(pyridine)iodonium tetrafluoroborate (379 mg, 1.02 mmol) was added to a solution of 4-(pyrimidin-2-ylmethyl)phenol (200 mg, 1.07 mmol) in 9:1 DCM:TFA (6 mL) at 0° C. The mixture was stirred for 1 h, partitioned between EtOAc and water, the layers were separated, and the organic layer was washed with satd. sodium thiosulfate. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 2-iodo-4-(pyrimidin-2-ylmethyl)phenol. MS (ESI) m/z: Calculated: 312.0; Observed: 313.0 (M++1).

Workup

  1. customat 0° C
  2. custompartitioned between EtOAc and water
  3. customthe layers were separated
  4. washthe organic layer was washed with satd
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-ca029ac172b44f40baf5a48e23649e17
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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