2,2,4-Trimethylpentane → HCID 57543426, compound

HRID 1641619Notes

Reaction equation

HRID 1641619 reaction equation
[CH:1]([CH2:4][C:5](C)(C)[CH3:6])([CH3:3])[CH3:2].[C:9]1([C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17](O)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:24]([O:27]CC)(=[O:26])[CH3:25].ClCCl>>[CH3:3][C:1]1[CH:2]=[C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[C:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:25]=2[C:24]([OH:27])=[O:26])[CH:17]=[C:5]([CH3:6])[CH:4]=1

Participants

4

Reactant 3

HCID 109072,2,4-TrimethylpentaneHCID 70357o-Phenylbenzoic acidHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 57543426HCID 57543426, compound

Procedure

Palladium acetate (5.6 mg, 0.025 mmol), 2-phenylbenzoic acid (99 mg, 0.5 mmol) and 3,5-dimethylchlorobenzene (211 mg, 1.5 mmol), butyldi-1-adamantylphosphine (19.2 mg, 0.05 mmol), Cs2CO3 (358 mg, 1.1 mmol), molecular sieves 3 Å (155 mg and anhydrous DMF (2.5 mL). After flash chromatography and preparative HPLC 101 mg (67%) of a white solid was obtained, mp 198-200° C. (isooctane). Rf-0.79 (1/9 ethyl acetate-dichloromethane). 1H NMR (300 MHz, CDCl3) δ 2.30 (s, 6H), 7.00 (s, 1H), 7.03 (s, 2H), 7.33-7.38 (m, 7H), 7.46-7.52 (m, 1H), 9.6 (br s, 1H). 1C NMR (75 MHz, CDCl3) δ 21.7, 122.5, 126.9, 128.1, 128.8, 129.0, 129.3, 129.5, 129.8, 130.0, 132.0, 138.3, 140.7, 141.0, 141.2, 174.2. FT-IR (neat, cm1) υ 1688, 1295. Anal. calcd for C21H18O2 (302.37 g/mol): C, 83.42; H, 6.00. Found: C, 83.13; H, 6.05. The 1H NMR spectrum of 2-phenylbenzoic acid is shown in FIG. 41. The 1H NMR and 13C NMR spectra of the product are shown in FIGS. 42A&E, respectively.

Sources & evidence

ORD record
ord-61713dfd5b3a4bd59a15f036ae8908da
Source dataset
uspto-grants-2012_02
Patent number
US08114993B2

Reaction notes

Loading…