Benzyl Bromide → HCID 57842865, compound

HRID 735496Notes

Reaction equation

HRID 735496 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13]OC1C=CC(B(O)O)=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B:24]([C:27]1[CH:32]=[CH:31][C:30](CCCC(O)=O)=[CH:29][CH:28]=1)([OH:26])[OH:25].C(Br)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C:30]1[CH:31]=[CH:32][C:27]([B:24]([OH:26])[OH:25])=[CH:28][CH:29]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 578425984-(4-Boronophenyl)butanoic acidHCID 578426684-(3-Benzyloxycarbonyl-propoxy)-phenylboronic acid

Product 1

HCID 57842865HCID 57842865, compoundYield 69%

Procedure

Using a procedure analogous to that used to prepare 1B, 2B (212 mg, 1:1 mixture of 2B and 2A) was reacted with benzyl bromide to afford 2C (90 mg, 69%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.92 (m, 2H), 2.33 (t, J=7.0 Hz, 2H), 2.62 (t, 2H), 5.08 (s, 2H), 7.11 (d, 2H), 7.25-7.35 (m, 5H), 7.69 (d, 2H).

Sources & evidence

ORD record
ord-d632fe29b5b24a96aeaaec4267b90ff2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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