Pivalic acid → HCID 69672702, compound

HRID 1751389Notes

Reaction equation

HRID 1751389 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC(C)(C)C(O)=O.Br[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1>CN(C)C(=O)C.FC1C=CC(P(C2C=CC(F)=CC=2)C2C=CC(F)=CC=2)=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=3)[O:23][CH2:22][C:16]=2[CH:17]=1

Participants

6

Reactant 3

HCID 6417Pivalic acidHCID 11430Potassium CarbonateHCID 69673054HCID 69673054, compound

Product 1

HCID 69672702HCID 69672702, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 140387Tris(4-fluorophenyl)phosphineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a degassed mixture of potassium carbonate (1.27 g, 9 mmol), palladium(II)trimethyl acetate (47 mg, 0.15 mmol), tris(p-fluorophenyl)phosphine (48 mg, 0.15 mmol) and trimethylacetic acid (93 mg, 0.9 mmol) was added 1-bromo-4-chloro-2-((3-methoxyphenoxy)methyl)benzene (1 g, 3 mmol) in N,N-dimethylacetamide (14 mL). The reaction was heated to 60° C. under argon for 18 hours. Upon completion, the reaction mixture was cooled to room temperature. The products were loaded directly onto a silica gel packed column and eluted using Hexanes/ethyl acetate to yield 8-chloro-3-methoxy-6H-benzo[c]chromene (739 mg, 98%)

Workup

  1. temperatureUpon completion, the reaction mixture was cooled to room temperature
  2. washeluted

Sources & evidence

ORD record
ord-087308e170714dd29568023c5579a0af
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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