Boron tribromide → HCID 22285658, compound

HRID 1062478Notes

Reaction equation

HRID 1062478 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 (APCI−) 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-4d0884ad7bcc404c8da48b48ca0c0f5e
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

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