Carbon tetrabromide → Ethyl (+/-)-4-(4-bromomethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

HRID 989900Notes

Reaction equation

HRID 989900 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([CH2:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:42]>C1COCC1>[Br:42][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23389065Ethyl (+/-)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

Product 1

HCID 23389064Ethyl (+/-)-4-(4-bromomethyl-1,3-oxazol-2-yl)-3-phenylbutanoateYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (±)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate (1.3 g, 4.49 mmole) in dry THF (20 mL) was added PPh3 (1.41 g, 5.39 mmole) then CBr4 (1.79 g, 5.39 mmole) at 0° C. After 20 min, the mixture was warmed to RT. After 2 hr, the mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel (20% EtOAc/hexanes) to give the title compound (1.38 g, 87%) as a colorless oil: MS (ES) m/e 352 (M+H)+.

Workup

  1. customat 0° C
  2. waitAfter 2 hr
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4487bf8119834a93a299f654a05b4b36
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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