Carbon tetrabromide → 1-Cyclopropyl-2-(2,2-dibromo-vinyl)-3-methyl-benzene

HRID 254552Notes

Reaction equation

[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[CH:6]=O)[CH2:3][CH2:2]1.[C:13](Br)(Br)([Br:15])[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[CH:6]=[C:13]([Br:15])[Br:14])[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 589517602-Cyclopropyl-6-methyl-benzaldehyde

Product 1

HCID 589517431-Cyclopropyl-2-(2,2-dibromo-vinyl)-3-methyl-benzene

Procedure

1-Cyclopropyl-2-(2,2-dibromo-vinyl)-3-methyl-benzene was prepared from 2-cyclopropyl-6-methyl-benzaldehyde, carbon tetrabromide and triphenylphosphine in analogy to Example 1d): colourless oil; 1H-NMR (CDCl3): 0.69 (2H, m, CH2), 0.94 (2H, m, CH2), 1.87 (1H, m, CH), 2.26 (3H, s, CH3), 6.77 (1H, d, ArH), 7.03 (1H, d, ArH), 7.17 (1H, t, ArH), 7.52 (1H, s, CH═CBr2).

Sources & evidence

ORD record: ord-0914288bb23b4abe9e751b8826947293
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875645B2

Reaction notes

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