Carbon tetrabromide → 6-(Bromomethyl)-2-methylbenzoxazole

HRID 1888782Notes

Reaction equation

HRID 1888782 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][C:5]=2[N:6]=1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br:14][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[O:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15662270(2-Methyl-1,3-benzoxazol-6-yl)methanol

Product 1

HCID 670157966-(Bromomethyl)-2-methylbenzoxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (2-methyl-1,3-benzoxazol-6-yl)methanol (66.5 mg, 0.408 mmol) in toluene (1 mL) were added carbon tetrabromide (135 mg, 0.408 mmol) and triphenylphosphine (106 mg, 0.408 mmol) and the mixture was stirred at room temperature for 30 min. The reaction mixture was directly applied to silica gel, and concentrated to dryness to give 6-(bromomethyl)-2-methyl-1,3-benzoxazole as an oil. To the obtained oil (92.0 mg, 0.408 mmol) were added DMF (4 mL), N-[1-(5-hydroxy-1-benzofuran-2-yl)ethyl]acetamide (30.0 mg, 0.136 mmol) obtained in Reference Example 38 and potassium carbonate (37.8 mg, 0.274 mmol), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was directly purified by basic silica gel column chromatography (hexane:ethyl acetate-4:1 to 3:7), and the solvent was evaporated. The residue was triturated with a small amount of ethyl acetate and diethyl ether to give the title compound (17.8 mg, yield 36%) as a white solid.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-241508f24f9f4b3eba7205dca8a5f63e
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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