Benzyl Bromide → 5-Allyl-4-(benzyloxy)-6-chloroindane

HRID 13946Notes

Reaction equation

[CH2:1]([C:4]1[C:12]([Cl:13])=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[OH:14])[CH:2]=[CH2:3].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:1]([C:4]1[C:5]([O:14][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[CH2:9][CH2:8][CH2:7]2)[CH:2]=[CH2:3]

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 24758Sodium hydride

HCID 685858685-Allyl-6-chloroindan-4-ol

Product 1

HCID 685842705-Allyl-4-(benzyloxy)-6-chloroindaneYield 89.2%

Procedure

Treatment of 5-allyl-6-chloroindan-4-ol (4.5 g, 0.0216 mol) with sodium hydride (60 wt. %, 1.32 g, 0.033 mol) followed by benzyl bromide (6.0 g, 0.035 mol) generally according to the procedure described for Intermediate 38 gave 5.76 g (89%) of 5-allyl-4-(benzyloxy)-6-chloroindane as a colorless oil. 1H NMR (CDCl3) 8H 7.40 (m, 5H); 7.05 (s, 1H); 6.00 (m, 1H); 5.00(m, 2H); 4.90 (s, 2H); 3.53 (dd, 2H); 2.90 (m, 4H); 2.05 (m, 2H).

Sources & evidence

ORD record: ord-45402095ab7d402f83ad407b94806d78
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Reaction notes

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