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

HRID 1422145Notes

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-983363f6fcd943e9aa17f0ace0e5a2f2
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080773

Reaction notes

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