Cesium carbonate → 3-(Hydroxymethyl)-4-m-tolyl-1H-isochromen-1-one

HRID 634354Notes

Reaction equation

HRID 634354 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH2:13][OH:14].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:14][CH2:13][C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:17]1[CH:16]=[C:15]([CH3:24])[CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27339503-Tolylboronic acidHCID 160500224-bromo-3-(hydroxymethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181311163-(Hydroxymethyl)-4-m-tolyl-1H-isochromen-1-oneYield 40.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was made in a similar way as that of the intermediate B2 using 4-bromo-3-(hydroxymethyl)-1H-isochromen-1-one (Intermediate A1, 0.5 g, 1.96 mmol), m-tolylboronic acid (0.400 g, 2.94 mmol), Pd(PPh3)4 (0.113 g, 0.098 mmol) and Cs2CO3 (0.64 g, 1.96 mmol) to afford the title compound (0.21 g, 40%).

Sources & evidence

ORD record
ord-a0711e45b1de46959e6e5f211da5945a
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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