4-Bromo-2-methyl-1-phenoxybenzene → 2-Methyl-4-(4,4,5,5-tetrametyl-1,3,2-dioxaborolan-2-yl)phenyl phenyl ether

HRID 51582Notes

Reaction equation

HRID 51582 reaction equation
BrC1C=CC(OC2C=CC=CC=2)=C(C)C=1.[O:16]([C:23]1[CH:30]=[CH:29][C:28]([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)=[CH:27][C:24]=1[C:25]#N)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCCC.C(OCC)(=O)C>[C:17]1([O:16][C:23]2[CH:30]=[CH:29][C:28]([B:31]3[O:35][C:34]([CH3:36])([CH3:37])[C:33]([CH3:39])([CH3:38])[O:32]3)=[CH:27][C:24]=2[CH3:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 227362534-Bromo-2-methyl-1-phenoxybenzeneHCID 227363402-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile

Product 1

HCID 669155832-Methyl-4-(4,4,5,5-tetrametyl-1,3,2-dioxaborolan-2-yl)phenyl phenyl ether

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in a 77% from 4-bromo-2-methyl-1-phenoxybenzene in a similar manner to that described for the preparation 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 7.67(s, 1H), 7.50(d, 1H), 7.38(t, 2H), 7.14(t, 1H), 6.94(d, 2H), 6.80(d, 1H), 2.21(t, 3H); TLC (heptane/ethyl acetate 9:1) Rf0.6.

Sources & evidence

ORD record
ord-693f2654c9d3446ba4e01380a9ba9440
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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