Boron tribromide → 2-Ethyl-5-(2-phenylethenyl)-1,3-benzenediol

HRID 252324Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:11]C)[C:8]=1[CH2:9][CH3:10].B(Br)(Br)Br>>[CH2:9]([C:8]1[C:7]([OH:11])=[CH:6][C:5]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][C:3]=1[OH:2])[CH3:10]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 66842591(E)-2-ethyl-1,3-dimethoxy-5-styrylbenzene

Product 1

HCID 1331902-Ethyl-5-(2-phenylethenyl)-1,3-benzenediolYield 91%

Procedure

This material was synthesized from 1-(3,5-dimethoxy-4-ethylphenyl)-2-phenylethene and BBr3 in 91% yield by the same method as described in Example 6. 1HNMR (CDCl3, ppm): δ 1.22 (t, J=7.5 Hz, 6H), 2.70 (q, J=7.5 Hz, 2H), 4.81 (s, 2H), 6.60 (s, 2H), 7.00 (s, 2H), 7.26 (m, 1H), 7.36 (m, 2H), 7.52 (m, 2H).

Sources & evidence

ORD record: ord-9442e234075b4b7b867d000a13cec3a9
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868047B2

Reaction notes

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