Benzonitrile, 4-bromo- → 4-(4-Cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1643642Notes

Reaction equation

HRID 1643642 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=N[C:20]([C:23](=O)N(C)C)=[CH:21][CH:22]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].BrC1C=CC([C:33]#[N:34])=CC=1.COC(C1C=C(O)C2CC(C)(C)OC=2C=1)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[CH:23][C:20]([C:33]#[N:34])=[CH:21][CH:22]=2)[C:8]2[CH2:9][C:10]([CH3:12])([CH3:13])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 595602244-(6-Dimethylcarbamoyl-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 667558044-(4-Cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 161b, from 4-bromo benzonitrile (246 mg, 1.35 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (300 mg, 1.35 mmol) to give a white foam (257 mg, 59% yield). 1H NMR (400 MHz, CDCl3) δ 7.58-7.71 (m, 2 H) 7.20-7.30 (m, 2 H) 6.95-7.06 (m, 2 H) 3.88 (s, 3 H) 2.88 (s, 2 H) 1.49 (s, 6 H); LCMS for C19H17NO4 m/z 324.00 (M+H+).

Sources & evidence

ORD record
ord-d0f620b2d2d4444aa6ec4b6e8faa4315
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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