Methanol → HCID 135830955, compound

HRID 1824785Notes

Reaction equation

HRID 1824785 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][C:12]=3[Cl:19])[O:10][C:6]=2[CH:5]=[C:4]([O:20]C)[CH:3]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=3[Cl:19])[O:10][C:6]=2[CH:5]=[C:4]([OH:20])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 22144508HCID 22144508, compound

Product 1

HCID 135830955HCID 135830955, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-chloro-2-(2-chloro-4-methoxy-phenyl)-6-methoxybenzooxazole (52 mg) in CH2Cl2 (2 mL) placed in and ice water bath was added drop wise 1.0 M BBr3 in CH2Cl2 (0.96 mL, 6 eq). After the reaction stirred over night, the mixture was placed in an ice water bath and excess MeOH was added drop wise to quench excess BBr3 and the mixture was stirred for an additional 20 min and concentrated. Flash chromatography on silica gel eluting with 0% to 40% ethyl acetate-hexane afforded 35 mg (74%) of the title compound as a solid. MS: 296 (MH+), HPLC tR: 2.32 min.

Workup

  1. customthe mixture was placed in an ice water bath
  2. customto quench excess BBr3
  3. stirringthe mixture was stirred for an additional 20 min
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f787adf9c8784f67ac26bbba9143970d
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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