Boron tribromide → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-hydroxy-N-nonyl-benzamide
Reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:25]([Cl:32])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:23]C)=[C:9]([CH:22]=1)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:11].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:25]([Cl:32])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:23])=[C:9]([CH:22]=1)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:11]Participants
4
Procedure
To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-N-nonyl-benzamide (173 mg, 0.36 mmol) in CH2Cl2 (3 ml) was added a solution of BBr3 (0.72 ml of a 1 M solution in CH2Cl2). The resulting mixture was stirred at RT for 1.5 h then quenched by addition of MeOH (1 ml) and water (10 ml). The resulting mixture was stirred at RT for 30 min then further diluted with 1 M HCl (10 ml) and extracted with CH2Cl2 (3×5 ml). The combined CH2Cl2 extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound of Step D (168 mg) as a viscous oil. The title product of Step D was used in the next step without further purification. MS (APCl−) Calc.: 468.1, Found: 467.2 (M−1).
Workup
- customthen quenched by addition of MeOH (1 ml) and water (10 ml)
- stirringThe resulting mixture was stirred at RT for 30 min
- additionthen further diluted with 1 M HCl (10 ml)
- extractionextracted with CH2Cl2 (3×5 ml)
- washThe combined CH2Cl2 extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a8c4375ac0234ec3ad893ba7807499c0
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664291B2
Reaction notes
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