Diethyl Ether → N-Benzyl-3-hydroxy-5-iodo-benzamide

HRID 1670070Notes

Reaction equation

HRID 1670070 reaction equation
[CH2:1]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[C:14]([O:16]C)[CH:13]=[C:12]([I:18])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(OCC)C>ClCCl.C(=O)=O.CC(C)=O>[CH2:1]([NH:8][C:9](=[O:19])[C:10]1[CH:11]=[C:12]([I:18])[CH:13]=[C:14]([OH:16])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 57905830N-benzyl-3-iodo-5-methoxy-benzamide

Product 1

HCID 57905909N-Benzyl-3-hydroxy-5-iodo-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18522661Acetone cardiceSolvent

Procedure

A solution of N-benzyl-3-iodo-5-methoxy-benzamide (4.7 g) in anhydrous dichloromethane (100 mL) was cooled to −78° C. in dry ice/acetone bath under flow of argon and a BBr3 solution (38.4 mL of 1 M solution in dichloromethane) was added dropwise. After the addition was completed, the reaction mixture was stirred at room temperature overnight. The reaction mixture was cooled in an ice bath and then quenched by a dropwise addition of methanol. Then it was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and concentrated to remove the solvents. The title compound was obtained by trituration with diethyl ether and hexanes (4.1 g, 90% yield).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customquenched by a dropwise addition of methanol
  4. additionThen it was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto remove the solvents

Sources & evidence

ORD record
ord-3374d53e150c4a28b06d3cf01f46ad1e
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

Loading…