Boron tribromide → HCID 69967032, compound

HRID 2305967Notes

Reaction equation

HRID 2305967 reaction equation
[CH3:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[C:20]([CH3:27])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:18]C)=[C:9]([S:11]([CH2:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1.B(Br)(Br)Br>>[CH:15]1([CH2:14][S:11]([C:9]2[CH:10]=[C:5]([O:4][C:3]3[C:2]([CH3:1])=[CH:23][C:22]([N+:24]([O-:26])=[O:25])=[CH:21][C:20]=3[CH3:27])[CH:6]=[CH:7][C:8]=2[OH:18])(=[O:13])=[O:12])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 18433434HCID 18433434, compound

Product 1

HCID 69967032HCID 69967032, compound

Procedure

2-Cyclopropylmethanesulfonyl-4-(2,6-dimethyl-4-nitro-phenoxy)-phenol was prepared from 5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-cyclopropylmethanesulfonylbenzene according to a procedure analogous to that described in EXAMPLE 2, Step B. Boron tribromide (1M in dichloromethane, 2.0 equiv) was used. After 30 minutes, ice water (50 ml) was added to quench the reaction, and the mixture was extracted with dichloromethane (3×25 ml). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was dissolved in ethyl acetate/methanol and stirred with activated carbon, then filtered through Celite® and concentrated. The title product of Step C was used in the next step without further purification. MS (APCI−) Calc.: 377.4, Found: 376.1 (M−1).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with dichloromethane (3×25 ml)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethyl acetate/methanol
  8. filtrationfiltered through Celite®
  9. concentrationconcentrated
  10. customThe title product of Step C was used in the next step without further purification

Sources & evidence

ORD record
ord-cb7f14b7d6444f9a9baa36d91148a03f
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

Loading…