1-Fluoro-3-iodobenzene → HCID 16110639, compound

HRID 605615Notes

Reaction equation

HRID 605615 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.FC1C=CC=C(I)C=1>>[F:33][C:29]1[CH:28]=[C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 707251-Fluoro-3-iodobenzeneHCID 16110607HCID 16110607, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110639HCID 16110639, compoundYield 98%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-Phenylheptyl)-5-(3-fluorophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (75 mg, 0.113 mmol) and 1-fluoro-3-iodobenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a clear oil (53 mg, 98%): 1H NMR (CDCl3, 400 MHz) 7.43-7.33 (m, 3H), 7.29-7.25 (m, 3H), 7.18-7.15 (m, 3H), 7.04-7.00 (m, 1H), 4.83 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.6 Hz), 1.96-1.88 (m, 2H), 1.63-1.59 (m, 2H), 1.47-1.35 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 170.4, 167.3 (d, J=245 Hz), 155.1, 147.9, 135.6 (d, J=8.4 Hz), 135.2 (d, J=8.5 Hz), 133.5, 133.3, 130.7, 127.7, 124.9 (d, J=3.0 Hz), 120.2 (d, J=21.1), 116.2 (d, J=23.5), 73.8, 41.5, 41.0, 36.5, 34.3, 34.3, 30.8, 30.2, 23.3, 0.2, 0.0.

Sources & evidence

ORD record
ord-a958061e266549e495e64bce8470b24b
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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