Toluene → 3-(3-Bromopropyl)-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde

HRID 590381Notes

Reaction equation

HRID 590381 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3]1.[Br:13][CH2:14][CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:13][CH2:14][CH2:15][CH2:16][N:6]1[C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3][C:2]1=[O:1]

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 3914742-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde2×HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 895538013-(3-Bromopropyl)-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehydeYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 290 mg (1.64 mmol) of 2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde (Intermediate 7), 272.8 mg (1.96 mmol) of 3-bromo-propan-1-ol, 514 mg (1.96 mmol) of triphenylphospine and 0.855 ml (1.96 mmol) of 40% toluene solution of DEAD in 7 ml THF is stirred overnight. After concentration in vacuo the residue is chromatographically purified over silicagel eluting with hexane/ethyl ether (100/0 to 0/100), obtaining 423 mg of the title product (58% purity; 52% total yield) that is used per se in the next synthetic step.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. customis chromatographically purified over silicagel
  3. washeluting with hexane/ethyl ether (100/0 to 0/100)

Sources & evidence

ORD record
ord-8c5283e17faf47ab8f197ea2fceea0bc
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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