Triphenylphosphine → 5-Chloro-2-benzofuranmethanamine

HRID 1772280Notes

Reaction equation

HRID 1772280 reaction equation
[N:1]([CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:8]=2[CH:9]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1.O>[Cl:14][C:11]1[CH:12]=[CH:13][C:7]2[O:6][C:5]([CH2:4][NH2:1])=[CH:9][C:8]=2[CH:10]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86719518HCID 86719518, compound

Product 1

HCID 623786725-Chloro-2-benzofuranmethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(azidomethyl)-5-chloro-1-benzofuran (500 mg, 2.44 mmol) in tetrahydrofuran (10 ml) and water (1 ml) was added PPh3 (759 mg, 2.89 mmol) and the contents were stirred for 3 hours at 60° C. The resulting mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography eluting with methanol in dichloromethane to afford (5-chloro-1-benzofuran-2-yl)methanamine as a colorless liquid (420 mg, crude). (ES, m/z): [M+H]+ 182.0; 1H NMR (400 MHz, CDCl3): δ 7.55-7.58 (m, 1H), 7.50-7.47 (m, 1H), 7.21 (d, J=8.8 Hz, 1H), 6.50 (s, 1H), 3.99 (s, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by silica gel column chromatography
  4. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-106aae31374c41e0adcf3dec3a4371ef
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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