Trimethyltin chloride → 2-(Benzo[d]oxazol-2-yl)benzaldehyde

HRID 428040Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)CCC.C([Sn](Cl)(CCCC)CCCC)CCC.C[Sn](Cl)(C)C.Br[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]>C1(C)C(C)=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 12.5 g of 2-tributylstannylbenzoxazole (prepared by the method of P. Jutzi and W. Gilge, J. Organometallic Chem. 1983, 246, 159, using tributyltin chloride as a less toxic replacement for trimethyltin chloride) 5.66 g 2-bromobenzaldehyde, and 0.46 g tetrakis(triphenylphosphine)-palladium (0) in 300 ml of anhydrous xylene under a nitrogen atmosphere was heated to 115° C. for 12 h. The reaction mixture was cooled to room temperature and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5) to afford 5.8 g of 2-(benzoxazol-2-yl)benzaldehyde, GC-M.S. (E.I.) (M/Z): 223 [M+].

Workup

customprepared by the method of P
temperatureThe reaction mixture was cooled to room temperature
customevaporated to dryness under reduced pressure
customThe resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5)

Sources & evidence

ORD record: ord-a7e3dc93c7464dd4b7789e0929315555
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313139B1

Reaction notes

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