2,6-Lutidine → 4-(Benzoxazol-2-yl)benzyl bromide

HRID 234739Notes

Reaction equation

HRID 234739 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14]O)=[CH:12][CH:11]=1.S(Br)([Br:20])=O.N1C(C)=CC=CC=1C>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][Br:20])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 68176Thionyl bromideHCID 153890174-(Benzoxazol-2-yl)benzyl alcohol

Product 1

HCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-(benzoxazol-2-yl)benzyl alcohol (20.9 g; 100 mmol) dissolved in CH2Cl2 (330 ml) and cooled to 0°-5° C. is added thionyl bromide (9.2 ml; 120 mmol) and allowed to warm to room temperature after removing the bath. After 11/2 hours, 2,6-lutidine (11.6 ml; 100 mmol) is added to the mixture and warmed to 30° C. The reaction mixture is then diluted with CH2Cl2, washed with H2O 1×, 0.2M HCl 1×, NaHCO3 2×, brine, dried (MgSO4) and concentrated to dryness. The residue is recrystallized from EtOAc to obtain 4-(benzoxazol-2-yl)benzyl bromide as white-orange needles which is used directly in Step E.

Workup

  1. temperaturecooled to 0°-5° C.
  2. customafter removing the bath
  3. temperaturewarmed to 30° C
  4. washwashed with H2O 1×, 0.2M HCl 1×, NaHCO3 2×, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customThe residue is recrystallized from EtOAc

Sources & evidence

ORD record
ord-c2d068af99cd464380045043b791571a
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

Loading…