Benzyl Alcohol → HCID 58387590, compound

HRID 1028062Notes

Reaction equation

HRID 1028062 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[C:15]2Cl>CN(C=O)C>[CH2:3]([O:10][C:15]1[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([Br:11])[CH:13]=2)[N:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 58387590HCID 58387590, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 60% NaH in mineral oil (1.75 equiv.) in DMF (0.5 M) was added benzyl alcohol (2.5 equiv.) dropwise. After stirring for 30 minutes, 6-bromo-4-chloroquinoline (1.0 equiv.) was added and the solution was heated in a microwave at 100° C. for 30 minutes. Upon cooling, the solution was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed further with H2O (3×) and NaCl(sat.), dried over MgSO4, concentrated and triturated with hexanes to yield 4-(benzyloxy)-6-bromoquinoline (73%). LC/MS=314.0/315.9 (M+H), LC=2.89 min.

Workup

  1. temperatureUpon cooling
  2. customthe solution was partitioned between EtOAc and H2O
  3. customUpon separation
  4. washthe organic layer was washed further with H2O (3×) and NaCl(sat.)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customtriturated with hexanes

Sources & evidence

ORD record
ord-b39e6799f9714236949b09e5a32e2ce6
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

Loading…