Bromobenzene → 7a-Phenyl-hexahydro-isobenzofuran-1-one

HRID 333276Notes

Reaction equation

HRID 333276 reaction equation
[C:1]1(=[O:10])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][O:2]1.[C:11]1(Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([C:9]23[C:1](=[O:10])[O:2][CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7961BromobenzeneHCID 3446531(3H)-Isobenzofuranone,hexahydro-

Product 1

HCID 589549237a-Phenyl-hexahydro-isobenzofuran-1-one

Procedure

The title compound was prepared from hexahydro-isobenzofuran-l-one (10 g, 1.3 eq) and phenyl bromide (5.4 mL, 51.27 mmol) according to General Procedure K. It was obtained as a clear oil (7.40 g, 67%). HPLC Rt (5-100-8)=9.8 min. 1H NMR (CDCl3, δ): 7.4-7.2 (m, 5H), 4.05 (dd, 1H), 3.90 (dd, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.8-1.3 (m, 6H). 13C NMR (CDCl3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).

Sources & evidence

ORD record
ord-198c6463f2fe404583fea36a82852d0c
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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