Triphenylphosphine → 3-(1,3-Dioxolan-2-yl)benzyl bromide

HRID 1198550Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C(N(CC)CC)C>[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][Br:1]

Participants

Conditions

Temperature: -5 °C

Procedure

Solid N-bromosuccinimide (10.4 g., 58 mmol) was added in small portions to a stirred solution of 3-(1,3-dioxolan-2-yl)benzyl alcohol (9.6 g., 53 mmol) and triphenylphosphine (16.7 g., 64 mmol) in dichloromethane (250 ml) at ca. -5° C. The yellow solution was stirred for a further 2 hours at -5° C. then added to a suspension of silica (50 g) in dichloromethane (250 ml) and triethylamine (2.5 ml). The mixture was evaporated and the residual silica was placed on the top of a silica column (250 g) and eluted with ethyl acetate-hexane (1:4) to give the product as a pale solid.

Workup

customThe mixture was evaporated
washeluted with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record: ord-08ea5fd0eb414bb589d58f8fa36a7c1f
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281593

Reaction notes

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