4-Fluorobenzyl bromide → HCID 178516655, compound

HRID 1506837Notes

Reaction equation

HRID 1506837 reaction equation
C([O-])(=O)C.[Na+].[SH:6][C:7]1[N:12]=[C:11]([OH:13])[CH:10]=[C:9]([OH:14])[N:8]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1>O.C(#N)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][S:6][C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[C:9]([OH:14])[N:8]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 517045Sodium AcetateHCID 178516656HCID 178516656, compound

Product 1

HCID 178516655HCID 178516655, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium acetate (113 g) was added to a suspension of 2-mercaptopyrimidine-4,6-diol (80 g) in water (900 mL) at room temperature. A solution of 1-(bromomethyl)-4-fluorobenzene (105 g) in acetonitrile (90 mL) was added dropwise over 2 hours. The reaction was allowed to stir for 20 hours before the suspension was filtered and washed with water (3×) and isohexane (3×). The solid was dried in vacuo for 2 hours and azeotroped with toluene (3×) to afford the sub-title product (125 g) as a white solid.

Workup

  1. filtrationwas filtered
  2. washwashed with water (3×) and isohexane (3×)
  3. customThe solid was dried in vacuo for 2 hours
  4. customazeotroped with toluene (3×)

Sources & evidence

ORD record
ord-afdf7c309fd242e191a108e46463e23d
Source dataset
uspto-grants-2015_12
Patent number
US09221782B2

Reaction notes

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