Water → HCID 59264722, compound

HRID 1891124Notes

Reaction equation

HRID 1891124 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[C:14]([C:16]2[O:20][N:19]=[C:18]([CH3:21])[C:17]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:13]([OH:30])=[CH:12][C:11]=1[OH:31].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.CCCCCC>[CH2:1]([O:30][C:13]1[CH:12]=[C:11]([O:31][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([Br:9])=[CH:15][C:14]=1[C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 136073675HCID 136073675, compound

Product 1

HCID 59264722HCID 59264722, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Benzyl bromide (0.36 ml, 3 mmol) was added suspension of 4-bromo-6-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzene-1,3-diol (Example 2) (0.55 g, 1.5 mmol) and cesium carbonate (0.85 g, 2.6 mmol) in DMF (5 ml) and the mixture stirred for ˜18 hrs, at room temperature. Water (100 ml) was added and the mixture extracted with diethyl ether (2×30 ml). The combined extracts were washed with water (4×75 ml) and saturated aqueous sodium chloride solution (50 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a pale brown gum. Trituration with hexane gave 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-3-methyl-isoxazole as an off-white solid, dried in vacuo, (0.5 g).

Workup

  1. extractionthe mixture extracted with diethyl ether (2×30 ml)
  2. washThe combined extracts were washed with water (4×75 ml) and saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialThe solution was dried over anhydrous magnesium sulphate
  4. concentrationconcentrated
  5. customto give a pale brown gum

Sources & evidence

ORD record
ord-6a2e9b1e070048949525cc48562278c0
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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