Boron Trichloride → HCID 135907040, compound

HRID 2097278Notes

Reaction equation

HRID 2097278 reaction equation
B(Cl)(Cl)Cl.C([O:12][C:13]1[CH:18]=[C:17]([O:19]CC2C=CC=CC=2)[C:16]([Br:27])=[CH:15][C:14]=1[C:28]1[C:32]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[C:31]([CH3:41])[O:30][N:29]=1)C1C=CC=CC=1>ClCCl>[Br:27][C:16]1[CH:15]=[C:14]([C:28]2[C:32]([C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)=[C:31]([CH3:41])[O:30][N:29]=2)[C:13]([OH:12])=[CH:18][C:17]=1[OH:19]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 59264710HCID 59264710, compound

Product 1

HCID 135907040HCID 135907040, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride solution (1M in dichloromethane, 1 ml, 1 mmol) was added to a solution of 3-(2,4-Bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-5-methyl-isoxazole (38 mg, 0.068 mmol) in dichloromethane (1 ml), and stirring was continued for 1 h. The reaction mixture was partitioned between water (20 ml) and dichloromethane (2×20 ml) and the combined organic phases were dried over anhydrous magnesium sulphate and concentrated in vacuo to leave a brown oil. The crude product was purified by column chromatography, silica (10 g), eluting with hexane, followed by hexane/diethyl ether (3:1 then 1:1), to give 4-Bromo-6-[4-(4-methoxy-phenyl)-5-methyl-isoxazol-3-yl]-benzene-1,3-diol as a colourless oil (11 mg, 43%).

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and dichloromethane (2×20 ml)
  2. dry with materialthe combined organic phases were dried over anhydrous magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customto leave a brown oil
  5. customThe crude product was purified by column chromatography, silica (10 g)
  6. washeluting with hexane

Sources & evidence

ORD record
ord-d731d49da31c4662be09d1c7bd9fa688
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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