Carbon tetrabromide → 1-Chloro-3-(2,2-dibromo-vinyl)-2-ethyl-4-fluoro-benzene

HRID 254569Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=O.[C:13](Br)(Br)([Br:15])[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[C:4]([CH:5]=[C:13]([Br:15])[Br:14])[C:3]=1[CH2:11][CH3:12]

Participants

Reactant 3

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 589517063-Chloro-2-ethyl-6-fluoro-benzaldehyde

Product 1

HCID 589517981-Chloro-3-(2,2-dibromo-vinyl)-2-ethyl-4-fluoro-benzene

Procedure

1-Chloro-3-(2,2-dibromo-vinyl)-2-ethyl-4-fluoro-benzene was prepared from 3-chloro-2-ethyl-6-fluoro-benzaldehyde, carbon tetrabromide and triphenylphosphine in analogy to Example 1d): colourless oil; 1H-NMR (CDCl3): 1.15 (3H, t, CH3), 2.72 (2H, q, CH2), 6.90 (1H, dd, ArH), 7.29 (1H, s, CH═CBr2), 7.33 (1H, dd, ArH).

Sources & evidence

ORD record: ord-6d12aff7c2e64937ac51fe6b07d7ee84
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875645B2

Reaction notes

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