Boron tribromide → HCID 22285658, compound

HRID 1168096Notes

Reaction equation

HRID 1168096 reaction equation
[CH:1]1([N:5]([CH3:28])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21]OC)=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25]C)[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:21][C:17]1[CH:18]=[C:19]([Cl:20])[C:14]([O:13][C:11]2[CH:10]=[CH:9][C:8]([OH:25])=[C:7]([CH:12]=2)[C:6]([N:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[CH3:28])=[O:27])=[C:15]([Cl:24])[CH:16]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22285660n-Cyclobutyl-5-(2,6-dichloro-4-methoxymethyl-phenoxy)-2-methoxy-n-methyl-benzamide

Product 1

HCID 22285658HCID 22285658, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of Step F in dichloromethane (2.2 ml) at room temperature was added boron tribromide (1M in dichloromethane, 1.5 ml, 1.5 mmol). The reaction mixture was stirred at room temperature for about two hours, and quenched with water (20 ml). After stirring for about 15 minutes, the solution was extracted with dichloromethane (3×15 ml). The combined organic extracts were washed with brine (50 ml), treated with activated carbon, filtered through diatomaceous earth, dried and concentrated to give the title compound (163 mg) as an off-white solid which was used in the next step without further purification. MS (APCl−) Calc: 457.0, found: 456.0 (M−1).

Workup

  1. customquenched with water (20 ml)
  2. stirringAfter stirring for about 15 minutes
  3. extractionthe solution was extracted with dichloromethane (3×15 ml)
  4. washThe combined organic extracts were washed with brine (50 ml)
  5. additiontreated with activated carbon
  6. filtrationfiltered through diatomaceous earth
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3d6ecfb4433c46859ce80a86f39c926b
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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