P-Anisidine → 7-t-Butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290151Notes

Reaction equation

HRID 2290151 reaction equation
Br[C:2]1[C:3]([CH3:17])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:4]1[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=[C:2]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[C:3]=1[CH3:17])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 7732P-AnisidineHCID 186991875-Bromo-7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran2×HCID 23676156Sodium t-butoxide

Product 1

HCID 186991917-t-Butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuranYield 99.1%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure K and using 5-bromo-7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 51, 0.33 g, 1.1 mmol), p-anisidine (0.25 g, 2 mmol), sodium tert-butoxide (0.2 g, 2.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.030 g, 0.03 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.060 g, 0.096 mmol) in 3 mL of anhydrous toluene, the title compound (0.37 g, quantitative yield) was obtained as a pink solid. 1H NMR (300 MHz, C6D6): δ 6.79 (d, 2H, J=8.9 Hz), 6.72 (s, 1H), 6.60 (d, 2H, J=8.7 Hz), 4.60 (br s, 1H), 3.90 (s, 2H), 3.35 (s, 3H), 2.37 (s, 3H), 1.68(s, 9H), 1.02 (s, 6H).

Sources & evidence

ORD record
ord-bd040e07d16d4db4b8b1f21832f24131
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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