Boron tribromide → HCID 18357354, compound

HRID 428346Notes

Reaction equation

HRID 428346 reaction equation
[CH:1]([N:4]([CH:22]([CH3:24])[CH3:23])[C:5](=[O:21])[CH2:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19]C)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:22]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:21])[CH2:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18357295N,N-Diisopropyl-3-(2-methoxyphenyl)-3-(2-thienyl)propanamide

Product 1

HCID 18357354HCID 18357354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-diisopropyl-3-(2-methoxyphenyl)-3-(2-thienyl)propanamide (2.37 g, 6.9 mmol) in dichloromethane(35 mL) was cooled down to −78° C. and boron tribromide (5.9 g 23.57 mmol) was added. The reaction mixture was allowed to slowly warm to room temperature. The reaction was quenched by slow addition of water (20 mL). The pH was adjusted to around 6 with NaHCO3(s) and the mixture was extracted three times with CH2Cl2. The combined organic phases were washed once with brine, dried (MgSO4) and the solvent was evaporated. This crude product (2.46 g, 107%) was used without further purification. 1H NMR (CDCl3) δ1.05 (d, 3H), 1.20 (m, 6H), 1.35 (d, 3H), 3.16 (m, 2H), 3.4 (br, 1H), 4.0 (m, 1H), 5.24 (dd. 1H), 6.7-7.2 (m, 7H).

Workup

  1. customThe reaction was quenched by slow addition of water (20 mL)
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. washThe combined organic phases were washed once with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated
  6. customThis crude product (2.46 g, 107%) was used without further purification

Sources & evidence

ORD record
ord-92f8a40ce1394acf99cd240b899183c0
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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