Phosphorus tribromide → HCID 69022121, compound

HRID 1866908Notes

Reaction equation

HRID 1866908 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17]O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].CCOCC.C(Cl)Cl.P(Br)(Br)[Br:29]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][Br:29])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 21881112Ethyl ether methylene chlorideHCID 69023625HCID 69023625, compound

Product 1

HCID 69022121HCID 69022121, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 5-hydroxymethylindole-1-carbamic acid tert-butyl ester (0.51 g, 2.1 mmol) in 4:1 Et2O/CH2Cl2 (4 mL) was added PBr3 (0.2 mL, 2.2 mmol), and the reaction mixture was stirred for 40 min. The reaction mixture was diluted with CH2Cl2, washed a saturated solution of NaHCO3 (3×10 mL), dried (Na2SO4), filtered, and the solvent was removed under reduced pressure to provide 5-bromomethyl-indole-1-carbamic acid tert-butyl ester as a yellow solid (0.59 g, 93%). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=9 Hz, 1H), 7.68-7.62 (m, 2H), 7.33 (d, J=9 Hz, 1H), 6.60 (s, 1H), 4.68 (s, 2H), 1.67 (s, 9H).

Workup

  1. washwashed a saturated solution of NaHCO3 (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-274afb4b48e541aaa0770caad1e19804
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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