Imidazole → HCID 58005152, compound

HRID 1879254Notes

Reaction equation

HRID 1879254 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:35]Br.N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Br:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 1393595HCID 1393595, compound

Product 1

HCID 58005152HCID 58005152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0.5 M solution of (3′-bromobiphenyl-3-yl)methanol 94 in DCM was added to a 10 min. prestirred suspension of triphenylphosphine resin (1.6 eq.), Br2 (1.6 eq.) and 0.25 M solution of imidazole (1.7 eq.) in DCM. The reaction mixture was gently stirred at RT for 3 h. The resin was then filtered off and washed with DCM, the filtrate was evaporated to dryness to afford the title compound 95 (78% crude yield) as a brown oil. The material was used in the following step without further purification. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.90 (s, 1H), 7.86-7.82 (m, 1H), 7.76-7.70 (m, 1H), 7.70-7.65 (m, 1H), 7.65-7.60 (m, 1H), 7.55-7.49 (m, 2H), 7.47 (d, J 7.8, 1H), 4.81 (s, 2H).

Workup

  1. stirringThe reaction mixture was gently stirred at RT for 3 h
  2. filtrationThe resin was then filtered off
  3. washwashed with DCM
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f6ccc508c0fd49e3be4776c474511378
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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