1-Bromo-4-tert-butylbenzene → HCID 57589726, compound

HRID 1674480Notes

Reaction equation

HRID 1674480 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:11]([C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].CC(C)([O-])C.[Na+]>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].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([NH:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 3

HCID 775951-Bromo-4-tert-butylbenzeneHCID 38411022,3-Dihydro-1-benzofuran-5-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 57589726HCID 57589726, compound

Reagents, catalysts & solvents 3

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

Procedure

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 2,3-dihydro-1-benzofuran-5-amine (11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 4-tert-butyl bromobenzene (18.1 grams, 85 mmoles), tris(dibenzylideneacetone)dipalladium (0) (1.6 grams, 1.7 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (16.4 grams, 0.17 moles) and anhydrous toluene (100 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (150 mL). The combined organic layers were concentrated in vacuo to yield a dark solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 10 grams of the desired product as a white solid. 1H NMR (CDCl3) δ 7.25 (d, 2H), 6.95 (s, 1H), 6.85 (d, 3H), 6.7 (d, 1H), 5.4 (bs, 1H), 4.5 (t, 2H), 3.15 (t, 2H), 1.3 (s, 9H).

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condensor, and nitrogen inlet
  3. custom11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S
  4. temperatureThe contents of the flask were refluxed for three days
  5. filtrationand filtered through a pad of silica gel
  6. washThe silica gel pad was then eluted with dichloromethane (150 mL)
  7. concentrationThe combined organic layers were concentrated in vacuo
  8. customto yield a dark solid
  9. customThe solid was chromatographed on silica gel
  10. washeluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-88f53e20332d45e580c9d3d4f6e3d778
Source dataset
uspto-grants-2011_08
Patent number
US08003583B2

Reaction notes

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