Triphenylphosphine → (6-Benzyloxynaphthalen-2-ylmethyl)-triphenyl-phosphonium Bromide

HRID 48102Notes

Reaction equation

HRID 48102 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][Br:20])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[Br-:20].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][P+:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 219769172-Benzyloxy-6-bromomethyl-naphthalen

Product 1

HCID 20632177(6-Benzyloxynaphthalen-2-ylmethyl)-triphenyl-phosphonium BromideYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 2-benzyloxy-6-bromomethyl-naphthalen (18) (1 equi.), and triphenylphosphine (1.1 equi.) in DMF (0.6 mL/mmole was stirred at 95 C for 15 h, cooled to room temperature, and quenched with ethyl acetate. The resulting white solid of (6-benzyloxynaphthalen-2-ylmethyl)-triphenylphosphonium bromide (19) was filtered and washed with ethyl acetate. Yield 98%.

Workup

  1. customquenched with ethyl acetate
  2. filtrationThe resulting white solid of (6-benzyloxynaphthalen-2-ylmethyl)-triphenylphosphonium bromide (19) was filtered
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-20e0aff8f86642d8a7a609f7ea37c173
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Reaction notes

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