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

HRID 634351Notes

Reaction equation

HRID 634351 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(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][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:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 160500224-bromo-3-(hydroxymethyl)-1H-isochromen-1-one2×

Product 1

HCID 214632763-(Hydroxymethyl)-4-phenyl-1H-isochromen-1-oneYield 36%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was made in a similar way as that of the intermediate B1, starting from 4-bromo-3-(hydroxymethyl)-1H-isochromen-1-one (Intermediate A1, 0.8 g, 3.14 mmol), phenylboronic acid (0.467 g, 3.83 mmol), Pd(PPh3)4 (0.181 g, 0.379 mmol) and Cs2CO3 (3.29 g, 10.11 mmol) to afford the title compound (210 mg, 36%).

Sources & evidence

ORD record
ord-1414882b74254135b639688dbb015d93
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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