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

HRID 1608569Notes

Reaction equation

HRID 1608569 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 1 1/2 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 1x, 0.2M HCl 1x, NaHCO3 2x, 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 1x, 0.2M HCl 1x, NaHCO3 2x, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customThe residue is recrystallized from EtOAc

Sources & evidence

ORD record
ord-36eb4e78813a42ad8ba857635f3b0529
Source dataset
uspto-grants-1995_03
Patent number
US05395846

Reaction notes

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