Boron tribromide → HCID 68556350, compound

HRID 1967579Notes

Reaction equation

HRID 1967579 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][N:6]([C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32]C)=[C:28]([CH:34]([CH2:36][CH3:37])[CH3:35])[CH:27]=2)=[C:20]([Cl:38])[CH:19]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)=[O:8])C.B(Br)(Br)Br>C(Cl)Cl>[CH:34]([C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[OH:32])[O:25][C:21]1[C:20]([Cl:38])=[CH:19][C:18]([N:6]([CH2:5][C:4]([OH:39])=[O:3])[C:7]([O:9][C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)=[O:8])=[CH:23][C:22]=1[Cl:24])([CH2:36][CH3:37])[CH3:35]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24954235HCID 24954235, compound

Product 1

HCID 68556350HCID 68556350, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a solution of [[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-(4-methoxy-phenoxycarbonyl)-amino]-acetic acid ethyl ester (6.4 g, 0.01 mol) in CH2Cl2 (128 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 (boron tribromide) solution (44.44 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (30 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by column chromatography over flash silica gel (chloroform:methanol) gradient elution from 95:5 to 90:10 to give pure [[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-(4-hydroxy-phenoxycarbonyl)-amino]-acetic acid (3.3 g, 58% yield)

Workup

  1. customquenched with H2O
  2. customorganic phase was separated
  3. washwashed with H2O, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe crude product was purified by column chromatography over flash silica gel (chloroform:methanol) gradient elution from 95:5 to 90:10

Sources & evidence

ORD record
ord-444a55a6edb342a5ad1ab112bce3e26f
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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